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4. Internet use by patients with bipolar disorder: Results from an international multisite survey

Author

Bauer, Rita, Conell, Jörn, Glenn, Tasha, Alda, Martin, Ardau, Raffaella, Baune, Bernhard T., Berk, Michael, Bersudsky, Yuly, Bilderbeck, Amy, Bocchetta, Alberto, Bossini, Letizia, Castro, Angela M. Paredes, Cheung, Eric YW., Chillotti, Caterina, Choppin, Sabine, Del Zompo, Maria, Dias, Rodrigo, Dodd, Seetal, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Hernandez, Miryam Fernández, Garnham, Julie, Geddes, John, Gildebro, Jonas, Gonzalez-Pinto, Ana, Goodwin, Guy M., Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Kapur, Vaisnvy, Kunigiri, Girish, Lafer, Beny, Larsen, Erik R., Lewitzka, Ute, Licht, Rasmus W., Lund, Anne Hvenegaard, Misiak, Blazej, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, Nielsen, René E, O’Donovan, Claire, Okamura, Yasushi, Osher, Yamima, Piotrowski, Patryk, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz K., Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, Scippa, Ângela M., Slaney, Claire, Sulaiman, Ahmad H., Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Vieta, Eduard, Vinberg, Maj, Viswanath, Biju, Volkert, Julia, Zetin, Mark, Whybrow, Peter C., and Bauer, Michael

Published
2016
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8. Online information seeking by patients with bipolar disorder: results from an international multisite survey

Author

Conell, Jörn, Bauer, Rita, Glenn, Tasha, Alda, Martin, Ardau, Raffaella, Baune, Bernhard T., Berk, Michael, Bersudsky, Yuly, Bilderbeck, Amy, Bocchetta, Alberto, Bossini, Letizia, Paredes Castro, Angela Marianne, Cheung, Eric Yat Wo, Chillotti, Caterina, Choppin, Sabine, Del Zompo, Maria, Dias, Rodrigo, Dodd, Seetal, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Garnham, Julie, Geddes, John, Gildebro, Jonas, Gonzalez-Pinto, Ana, Goodwin, Guy M., Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Kapur, Vaisnvy, Kunigiri, Girish, Lafer, Beny, Lam, Chun, Larsen, Erik Roj, Lewitzka, Ute, Licht, Rasmus, Lund, Anne Hvenegaard, Misiak, Blazej, Piotrowski, Patryk, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, Nielsen, René E., O’Donovan, Claire, Okamura, Yasushi, Osher, Yamima, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz K., Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, Scippa, Ângela Miranda, Slaney, Claire, Sulaiman, Ahmad Hatim, Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Vieta, Eduard, Vinberg, Maj, Viswanath, Biju, Volkert, Julia, Zetin, Mark, Zorrilla, Iñaki, Whybrow, Peter C., and Bauer, Michael

Published
2016
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9. Internet use by older adults with bipolar disorder: international survey results

Author

Bauer, Rita, Glenn, Tasha, Strejilevich, Sergio, Conell, Jörn, Alda, Martin, Ardau, Raffaella, Baune, Bernhard T., Berk, Michael, Bersudsky, Yuly, Bilderbeck, Amy, Bocchetta, Alberto, Castro, Angela M. Paredes, Cheung, Eric Y. W., Chillotti, Caterina, Choppin, Sabine, Cuomo, Alessandro, Del Zompo, Maria, Dias, Rodrigo, Dodd, Seetal, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Fernández Hernandez, Miryam, Garnham, Julie, Geddes, John, Gildebro, Jonas, Gitlin, Michael J., Gonzalez-Pinto, Ana, Goodwin, Guy M., Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Lund, Anne Hvenegaard, Kapur, Vaisnvy, Kunigiri, Girish, Lafer, Beny, Larsen, Erik R., Lewitzka, Ute, Licht, Rasmus W., Misiak, Blazej, Piotrowski, Patryk, Miranda-Scippa, Ângela, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, Nielsen, René E., O’Donovan, Claire, Okamura, Yasushi, Osher, Yamima, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz K., Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, Slaney, Claire, Sulaiman, Ahmad H., Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Veeh, Julia, Vieta, Eduard, Vinberg, Maj, Viswanath, Biju, Zetin, Mark, Whybrow, Peter C., and Bauer, Michael

Published
2018
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11. Erratum to: Online information seeking by patients with bipolar disorder: results from an international multisite survey

Author

Conell, Jörn, Bauer, Rita, Glenn, Tasha, Alda, Martin, Ardau, Raffaella, Baune, Bernhard T., Berk, Michael, Bersudsky, Yuly, Bilderbeck, Amy, Bocchetta, Alberto, Bossini, Letizia, Paredes Castro, Angela Marianne, Cheung, Eric Yat Wo, Chillotti, Caterina, Choppin, Sabine, Del Zompo, Maria, Dias, Rodrigo, Dodd, Seetal, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Garnham, Julie, Geddes, John, Gildebro, Jonas, Gonzalez-Pinto, Ana, Goodwin, Guy M., Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Kapur, Vaisnvy, Kunigiri, Girish, Lafer, Beny, Lam, Chun, Larsen, Erik Roj, Lewitzka, Ute, Licht, Rasmus W., Lund, Anne Hvenegaard, Misiak, Blazej, Piotrowski, Patryk, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, Nielsen, René E., O’Donovan, Claire, Okamura, Yasushi, Osher, Yamima, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz K., Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, Scippa, Ângela Miranda, Slaney, Claire, Sulaiman, Ahmad Hatim, Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Vieta, Eduard, Vinberg, Maj, Viswanath, Biju, Volkert, Julia, Zetin, Mark, Zorrilla, Iñaki, Whybrow, Peter C., and Bauer, Michael

Published
2017
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17. Lithiation of 2-heterosubstituted pyridines with BuLi-LiDMAE: evidenve for regiospecificity at C-6

Author

Gros, Philippe, Choppin, Sabine, Mathieu, Julien, and Fort, Yves

Subjects
Chemistry, Organic -- Research, Lithium -- Physiological aspects, Pyridine -- Physiological aspects, Nitrogen -- Physiological aspects, Hydrogen -- Physiological aspects, Oxygen -- Physiological aspects, Carbon -- Physiological aspects, Chlorine -- Physiological aspects, Biological sciences, Chemistry
Abstract

Research has been conducted on the 2-chloro- and 2-methoxypyridine. The initial deprotonation site of these compounds during the reaction with BuLi-Me (sub)2 N(CH (sub)2) (sub)2 OLi has been determined and the details are reported.

Published
2002

21. Internet use by older adults with bipolar disorder: international survey results

Author

Bauer, Michael, Bauer, Rita, Glenn, Tasha, Strejilevich, Sergio, Conell, Jörn, Alda, Martin, Ardau, Raffaella, Baune, Bernhard T., Berk, Michael, Bersudsky, Yuly, Bilderbeck, Amy, Bocchetta, Alberto, Paredes Castro, Angela M., Cheung, Eric Y. W., Chillotti, Caterina, Choppin, Sabine, Cuomo, Alessandro, Del Zompo, Maria, Dias, Rofrigo, Dodd, Seetalq, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Fernández Hernandez, Miryam, Garnham, Julie, Geddes, John, Gildebro, Jonas, Michael J., Gonzalez-Pinto, Anna, Goodwin, Guy M., Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Hvenegaard Lund, Anne, Kapur, Vaisnvy, Kunigiri, Girish, Lafer, Beny, Larsen, Erik R., Lewitzka, Ute, Licht, Rasmus W., Misiak, Blazej, Piotrowski, Patryk, Miranda-Scippa, Angela, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, Nielsen, René E., O´Donovan, Claire, Okamura, Yasushi, Osher, Yamima, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz K., Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, Slaney, Claire, Sulaiman, Ahmad H., Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Veeh, Julia, Vieta, Eduard, Vinberg, Maj, Viswanath, Biju, and Whybrow, Peter C.

Subjects
bipolare Störung, Informationssuche, medizinische Begleiterkrankungen, endokrine, respiratorische und kardiovaskuläre Erkrankungen, Technische Universität Dresden, Publikationsfond, ddc:610, bipolar disorder, information seeking, medical comorbidities, endocrine, respiratory and cardiovascular conditions, Technische Universität Dresden, Publishing Funds
Abstract

Background: The world population is aging and the number of older adults with bipolar disorder is increasing. Digital technologies are viewed as a framework to improve care of older adults with bipolar disorder. This analysis quantifes Internet use by older adults with bipolar disorder as part of a larger survey project about information seeking. Methods: A paper-based survey about information seeking by patients with bipolar disorder was developed and translated into 12 languages. The survey was anonymous and completed between March 2014 and January 2016 by 1222 patients in 17 countries. All patients were diagnosed by a psychiatrist. General estimating equations were used to account for correlated data. Results: Overall, 47% of older adults (age 60 years or older) used the Internet versus 87% of younger adults (less than 60 years). More education and having symptoms that interfered with regular activities increased the odds of using the Internet, while being age 60 years or older decreased the odds. Data from 187 older adults and 1021 younger adults were included in the analysis excluding missing values. Conclusions: Older adults with bipolar disorder use the Internet much less frequently than younger adults. Many older adults do not use the Internet, and technology tools are suitable for some but not all older adults. As more health services are only available online, and more digital tools are developed, there is concern about growing health disparities based on age. Mental health experts should participate in determining the appropriate role for digital tools for older adults with bipolar disorder.

Published
2018

22. Transition-Metal-Free Synthesis of a Known Intermediate in the Formal Synthesis of (-)-Steganacin

Author

Augros, David, Yalcouye, Boubacar, Choppin, Sabine, Chessé, Matthieu, Panossian, Armen, Leroux, Frédéric R., Laboratoire de chimie moléculaire (LCM), and Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Abstract

International audience; The formal synthesis of both enantiomers of a natural axially chiral biaryl, steganacin is reported. The previously developed atropo-diastereoselective coupling of an aryne and an aryllithium (the 'ARYNE coupling') allows for this synthesis. In each step, the axial configuration of the biaryl could be maintained. The key intermediate of literature was accessed without using transition metals, demonstrating the interest of the ARYNE coupling as a complement or an alternative to transition metal-catalyzed couplings.

Published
2017

25. Unintended Formation of a 26-Membered Cycle in the Course of a Novel Approach to Myricanol, a Strained [7,0]-Metacyclophane.

Author

Massé, Paul, Choppin, Sabine, Chiummiento, Lucia, Hanquet, Gilles, and Colobert, Françoise

Subjects
*DIMERIZATION, *NATURAL products
Abstract

A convergent approach for the synthesis of (±)-myricanol, a strained diarylheptanoid isolated from Myricacae , was undertaken using a Suzuki–Miyaura coupling followed by a ring-closing metathesis (RCM). Herein, we report the unintentional formation of a 26-membered macrocycle as RCM product resulting from a head-to-tail dimerization of the seco -precursor, even in relay ring-closing metathesis (RRCM) conditions. [ABSTRACT FROM AUTHOR]

Published
2020
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33. Atropo-diastereoselective coupling of aryllithiums and arynes — variations around the chiral auxiliary

Author

Leroux, Frédéric R., Augros, David, Yalcouye, Boubacar, Berthelot-Bréhier, Anaïs, Chessé, Matthieu, Choppin, Sabine, Panossian, Armen, Leroux, Frédéric, Laboratoire d'innovation moléculaire et applications (LIMA), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Coupling, Chiral auxiliary, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, chemistry.chemical_element, Sulfoxide, Oxazoline, 010402 general chemistry, 01 natural sciences, Biochemistry, Aryne, 0104 chemical sciences, 3. Good health, Solvent, chemistry.chemical_compound, C c coupling, chemistry, Computational chemistry, Drug Discovery, Organic chemistry, Lithium, ComputingMilieux_MISCELLANEOUS
Abstract

The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection.

Published
2016

34. MOESM1 of Online information seeking by patients with bipolar disorder: results from an international multisite survey

Author

Jörn Conell, Bauer, Rita, Glenn, Tasha, Alda, Martin, Ardau, Raffaella, Baune, Bernhard, Berk, Michael, Yuly Bersudsky, Bilderbeck, Amy, Bocchetta, Alberto, Bossini, Letizia, Castro, Angela Paredes, Cheung, Eric, Chillotti, Caterina, Choppin, Sabine, Zompo, Maria, Dias, Rodrigo, Seetal Dodd, Duffy, Anne, Etain, Bruno, Fagiolini, Andrea, Garnham, Julie, Geddes, John, Gildebro, Jonas, Gonzalez-Pinto, Ana, Goodwin, Guy, Grof, Paul, Harima, Hirohiko, Hassel, Stefanie, Henry, Chantal, Hidalgo-Mazzei, Diego, Vaisnvy Kapur, Girish Kunigiri, Beny Lafer, Lam, Chun, Larsen, Erik, Lewitzka, Ute, Licht, Rasmus, Lund, Anne, Blazej Misiak, Piotrowski, Patryk, Monteith, Scott, Munoz, Rodrigo, Nakanotani, Takako, René Nielsen, O’Donovan, Claire, Okamura, Yasushi, Yamima Osher, Reif, Andreas, Ritter, Philipp, Rybakowski, Janusz, Sagduyu, Kemal, Sawchuk, Brett, Schwartz, Elon, ÂNgela Scippa, Slaney, Claire, Sulaiman, Ahmad, Suominen, Kirsi, Suwalska, Aleksandra, Tam, Peter, Tatebayashi, Yoshitaka, Tondo, Leonardo, Vieta, Eduard, Vinberg, Biju Viswanath, Volkert, Julia, Zetin, Mark, Iñaki Zorrilla, Whybrow, Peter, and Bauer, Michael

Subjects
mental disorders, sense organs
Abstract

Additional file 1. Questionnaire: Information seeking in bipolar disorder.

Published
2016
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35. International multi-site survey on the use of online support groups in bipolar disorder

Author

Bauer, Rita, primary, Conell, Jörn, additional, Glenn, Tasha, additional, Alda, Martin, additional, Ardau, Raffaella, additional, Baune, Bernhard T., additional, Berk, Michael, additional, Bersudsky, Yuly, additional, Bilderbeck, Amy, additional, Bocchetta, Alberto, additional, Bossini, Letizia, additional, Castro, Angela M. Paredes, additional, Cheung, Eric Y. W., additional, Chillotti, Caterina, additional, Choppin, Sabine, additional, Zompo, Maria Del, additional, Dias, Rodrigo, additional, Dodd, Seetal, additional, Duffy, Anne, additional, Etain, Bruno, additional, Fagiolini, Andrea, additional, Hernandez, Miryam Fernández, additional, Garnham, Julie, additional, Geddes, John, additional, Gildebro, Jonas, additional, Gonzalez-Pinto, Ana, additional, Goodwin, Guy M., additional, Grof, Paul, additional, Harima, Hirohiko, additional, Hassel, Stefanie, additional, Henry, Chantal, additional, Hidalgo-Mazzei, Diego, additional, Kapur, Vaisnvy, additional, Kunigiri, Girish, additional, Lafer, Beny, additional, Larsen, Erik R., additional, Lewitzka, Ute, additional, Licht, Rasmus W., additional, Hvenegaard Lund, Anne, additional, Misiak, Blazej, additional, Piotrowski, Patryk, additional, Monteith, Scott, additional, Munoz, Rodrigo, additional, Nakanotani, Takako, additional, Nielsen, René E, additional, O’donovan, Claire, additional, Okamura, Yasushi, additional, Osher, Yamima, additional, Reif, Andreas, additional, Ritter, Philipp, additional, Rybakowski, Janusz K., additional, Sagduyu, Kemal, additional, Sawchuk, Brett, additional, Schwartz, Elon, additional, Scippa, Ângela M, additional, Slaney, Claire, additional, Sulaiman, Ahmad H., additional, Suominen, Kirsi, additional, Suwalska, Aleksandra, additional, Tam, Peter, additional, Tatebayashi, Yoshitaka, additional, Tondo, Leonardo, additional, Vieta, Eduard, additional, Vinberg, Maj, additional, Viswanath, Biju, additional, Volkert, Julia, additional, Zetin, Mark, additional, Whybrow, Peter C., additional, and Bauer, Michael, additional

Published
2017
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38. ChemInform Abstract: Selective Claisen Rearrangement and Iodination for the Synthesis of Polyoxygenated Allyl Phenol Derivatives.

Author

Bochicchio, Antonella, primary, Cefola, Rossella, additional, Choppin, Sabine, additional, Colobert, Francoise, additional, Di Noia, Maria Antonietta, additional, Funicello, Maria, additional, Hanquet, Gilles, additional, Pisano, Isabella, additional, Todisco, Simona, additional, and Chiummiento, Lucia, additional

Published
2016
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40. Lithiation of 2-chloro- and 2-methoxypyridine with lithium dialkylamides: initial ortho-direction or subsequent lithium ortho-stabilization?

Author

Gros, Philippe, Choppin, Sabine, and Fort, Yves

Subjects
Chemistry, Organic -- Research, Chlorine compounds, Pyridine -- Composition, Amides -- Composition, Organic compounds -- Composition, Deuterium, Biological sciences, Chemistry
Abstract

Research has been conducted on 20chloro- and 2-methoxypyridin. The authors have investigated the lithiation pathway of these compounds with lithium dialkylamides via the use of deuterated probes.

Published
2003

41. Synthesis, characterization, and catalytic application in aldehyde hydrosilylation of half-sandwich nickel complexes bearing (κ1-C)- and hemilabile (κ2-C,S)-thioether-functionalised NHC ligands.

Author

Ulm, Franck, Poblador-Bahamonde, Amalia I., Choppin, Sabine, Bellemin-Laponnaz, Stéphane, Chetcuti, Michael J., Achard, Thierry, and Ritleng, Vincent

Subjects
HYDROSILYLATION, ALDEHYDES, METAL complexes
Abstract

Neutral nickel–N-heterocyclic carbene complexes, (κ1-C)-[NiCpBr{R-NHC-(CH2)2SR′}] [Cp = η5-C5H5; R-NHC-(CH2)2SR′ = 1-mesityl-3-[2-(tert-butylthio)ethyl]- (1a), 1-mesityl-3-[2-(phenylthio)ethyl]- (1b), 1-benzyl-3-[2-(tert-butylthio)ethyl]- (1c), 1-benzyl-3-[2-(phenylthio)ethyl]-imidazol-2-ylidene (1d)], which bear a N-bound thioether side arm, were prepared by the reaction of nickelocene with the corresponding imidazolium bromides [R-NHC-(CH2)2SR′·HBr] (a–d), via conventional or microwave heating. The 1H NMR spectra of the benzyl-substituted species 1c and 1d showed signals for diastereotopic NCH2CH2S protons at room temperature. However, structural studies established the absence of coordination of the sulphur atom in the solid state, and solvent DFT calculations showed that bromide displacement by sulphur is an unfavourable process (ΔG = +13.5 kcal mol−1 for 1d), thereby suggesting that the observed disatereotopicity is more likely due to significant steric congestion rather than to a possible C,S-chelation in solution. Treatment of these complexes with KPF6 in tetrahydrofuran (THF) led to bromide abstraction to afford the cationic complexes [NiCp{R-NHC-(CH2)2SR′}](PF6) (2a–c). Alternatively, 2a–c could also be prepared by the direct reaction of nickelocene with the corresponding imidazolium hexafluorophosphate salts [R-NHC-(CH2)2SR′·HPF6]. Inversely to the neutral species, whereas X-ray crystallography established C,S-chelation in the solid state, the 1H NMR spectra (CDCl3, CD2Cl2, or thf-d8) at room temperature showed no diastereotopic NCH2CH2S protons, thus suggesting the possible displacement of the sulphur atom by the respective solvents and/or very fast sulphur inversion. DFT calculations established a low energy inversion process in all cases (+9 ≤ΔG‡≤ +13 kcal mol−1) as well as a favourable solvent coordination process (ΔG‡≈ +11 kcal mol−1; ΔG≈−7 kcal mol−1) with a solvent such as THF, thus suggesting that sulphur inversion and/or solvent coordination can both account for the absence of diastereotopy at room temperature, depending on the solvent. While all complexes catalysed the hydrosilylation of benzaldehyde in the absence of any additive, the cationic C,S-chelated complexes 2 proved more active than the sterically constrained neutral species 1. In particular, 2c proved to be the most active pre-catalyst and its catalytic charge could be lowered down to 2 mol% with PhSiH3 as the hydrogen source. [ABSTRACT FROM AUTHOR]

Published
2018
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42. A concise atroposelective formal synthesis of (-)-steganone

Author

Yalcouye, Boubacar, Choppin, Sabine, Panossian, Armen, Leroux, Frédéric, Colobert-leuenberger, Francoise, Substances naturelles/chimie moléculaire, Université Louis Pasteur - Strasbourg I-Ecole européenne de chimie, polymères et matériaux [Strasbourg]-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA), Laboratoire d'innovation moléculaire et applications (LIMA), and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Abstract

The atroposelective formal synthesis of (-)-steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones, was reported. The synthesis features an atropo-diastereoselective biaryl Suzuki-Miyaura cross-coupling with ≤99% de using an enantiopure and efficiently converted β-hydroxy sulfoxide deriv. as chiral auxiliary.

Published
2014

48. FeCl3·6H2O/acetaldehyde, a versatile system for the deprotection of ketals and acetals via a transacetalization process.

Author

Schiavo, Lucie, Choppin, Sabine, Hanquet, Gilles, Jeanmart, Loïc, and Lanners, Steve

Subjects
*ACETALDEHYDE, *KETALS, *ACETAL resins
Abstract

Mild and efficient catalytic deprotection of ketals/acetals mediated by FeCl3·6H2O/acetaldehyde has been described in this paper. The versatility and high chemoselectivity of the iron(iii)/aldehyde system are demonstrated by a large scope of examples. Deprotected ketones/aldehydes are nearly quantitatively isolated after filtration over a pad of silica gel followed by evaporation of volatile by-products. [ABSTRACT FROM AUTHOR]

Published
2017
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50. Nouvelles superbases unimétalliques lithiées et sodées : réactivité vis-à-vis de l'allylphénylsulfure et des 2-, 3- et 4- chloropyridines

Author

Choppin, Sabine, UL, Thèses, Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Henri Poincaré - Nancy 1, and Yves Fort

Subjects
Bases (chimie), [PHYS.COND.CM-GEN] Physics [physics]/Condensed Matter [cond-mat]/Other [cond-mat.other], [PHYS.COND.CM-GEN]Physics [physics]/Condensed Matter [cond-mat]/Other [cond-mat.other], Lithium-Composés organiques, Amino-alcools, Liaisons covalentes
Abstract

Non disponible/Not avialable., Le travail présente dans ce mémoire a montré l'efficacité, la sélectivité ainsi que le potentiel synthétique de nouvelles superbases unimétalliques lithiées et sodées dans des réactions de métallation. La première partie est consacrée à la métallation de l'allylphenylsulfure par des superbases unimetalliques sodées et lithiées. Il a en particulier été montré que l'activation de NANH 2 par un amino-alcoolate de sodium permet d'obtenir une nouvelle réaction de bisfonctionnalisation directe du substrat. Cette réaction originale donne un accès aisé à des cétones dissymétriques. La recherche d'une explication au phénomène d'activation à montrer que l'amidure de sodium pouvait également être activé par une espèce non anionique, le DME. L'utilisation de superbases unimétalliques lithiées, N-BULI-ROLI, conduit à des systèmes d'efficacité et de sélectivité comparables à celles des systemes bimétalliques de type LICKOR ou les systèmes de type base/activant tel que N-BULI/DABCO. Dans une seconde partie, il a été montré que le système unimétallique lithie n-buli-dimethylaminoethylate de lithium noté N-BULI-LIDMAE permet d'accéder à une métallation-fonctionnalisation chimio- et regioséléctive en ortho de l'azote des chloropyridines. La méthodologie développée permet un accès original à des précurseurs de molécules polyhétérocycliques à activité biologique potentielle, d'agents chélatants et de ligands de métaux de transition. Des calculs théoriques et des expériences réalisées sur des espèces deuterées ont ensuite montré que le site initial de déprotonnation des 2-, 3- et 4-chloropyridines est probablement le site situé en alpha de l'azote pyridinique et ceci quel que soit le système basique utilisé. Par ailleurs, la formation d'agrégats au voisinage de cet azote pyridinique peut être rendue responsable de la stabilité particulière des lithiens issus des 2-, 3- et 4-chloropyridines en présence du système N-BULI-LIDMAE. Il a enfin été montré que les méthodes de métallation sélective par N-BULI-LIDMAE, couplées a des réactions pallado-catalysées de type negishi et stille permettent un accès original et très efficace à des composés polyhétérocycliques refonctionnalisables.

Published
2001

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