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Your search keyword '"Hurvois, Jean-Pierre"' showing total 166 results
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166 results on '"Hurvois, Jean-Pierre"'

1. Enantioselective Synthesis of Planar Chiral Ferrocene Triflones.

Author

Wen, Min, Erb, William, Mongin, Florence, Hurvois, Jean‐Pierre, Blot, Marielle, Roisnel, Thierry, Halauko, Yury S., Matulis, Vadim E., Koike, Yuta, Kitazawa, Yu, Kimura, Mutsumi, and Uchiyama, Masanobu

Subjects
AMIDES, TIME series analysis, CRYSTALLIZATION, CHELATES, CHIRALITY, FERROCENE
Abstract

A multi‐gram scale synthesis of ferrocenetriflone was optimised from ferrocenesulfonyl fluoride and Me3SiCF3 (Ruppert reagent). Enantioselective deprotolithiations were then optimised using alkyllithiums in the presence of catalytic (+)‐sparteine to afford 2‐substituted ferrocene triflones in 79–84% ee. The use of chiral lithium amides in the presence of in situ traps was also optimised and was found to outperform alkyllithium⋅chiral diamine chelates for the first time in the ferrocene series, with 89–93% ee. Crystallisation of derivatives afforded enantiopure compounds that were engaged in deprotolithiation‐electrophilic trapping sequences, a halogen 'dance' reaction and transition metal‐promoted coupling to afford a wide range of variously polysubstituted ferrocene triflones. [ABSTRACT FROM AUTHOR]

Published
2024
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6. From benzofuro-, benzothieno- and 10-methylindolo-[2,3-b]-fused benzothiopyrano[4,3,2-de]quinolines to the corresponding benzothiopyrano[4,3,2-de]1,8-naphthyridines: synthesis and properties of these hexacyclic heteroaromatic compounds

Author

Mast, Nicolas, primary, Erb, William, additional, Nauton, Lionel, additional, Moreau, Pascale, additional, Mongin, Olivier, additional, Roisnel, Thierry, additional, Macaigne, Margaux, additional, Robert, Thomas, additional, Bach, Stéphane, additional, Picot, Laurent, additional, Thiéry, Valérie, additional, Hurvois, Jean-Pierre, additional, and Mongin, Florence, additional

Published
2023
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11. Formal Synthesis of (-)-Perhydrohistrionicotoxin Using a Thorpe-Ziegler Cyclization Approach. Synthesis of Functionalized Aza-Spirocycles

Author

Vu, Van Ha, Bouvry, Christelle, Roisnel, Thierry, Golhen, Stéphane, Hurvois, Jean-Pierre, Vietnam Institute of Industrial Chemistry, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ministry of Education and Training of the Socialist Republic of Vietnam, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)

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

International audience; The formal synthesis of (–)‐PHTX is described. Our approach was based on the anodic cyanation of (S)‐1‐(1‐phenylethyl)‐piperidine (–)‐1 to afford α‐aminonitrile 2 in 85 % yield in a 53:47 dr. The presence of the α‐phenylethyl group as the chiral auxiliary ensured the control of the absolute configuration of the future C6 spiro‐center during the alkylation step of 2, which was carried out with 1‐bromo‐4‐chlorobutane. Next, elaboration of the 1‐azaspiro[5,5]undecane‐7‐one ring system was achieved in a two‐step sequence, involving (a) a Thorpe‐Ziegler annulation, and (b) the hydrolysis–decarboxylation of enaminonitrile (–)‐5 to afford spiroketone (+)‐6 in >99:1 dr. Finally, the incorporation of the future C7 butyl chain was carried out stereoselectively through a new reaction sequence which involved the synthesis of tricyclic oxazolidinone (–)‐11 and alkylation of the intermediary syn‐fluorohydrin (+)‐13 with nBuMgCl to form oxazolidinone (+)‐15 in an overall 19 % yield from (–)‐1.

Published
2019
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14. Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step

Author

Louafi, Fadila, Hurvois, Jean-Pierre, Chibani, Aissa, and Roisnel, Thierry

Subjects
Alkaloids -- Chemical properties, Alkylation -- Analysis, Amines -- Chemical properties, Methyl groups -- Chemical properties, Methyl groups -- Structure, Nitriles -- Chemical properties, Quinoline -- Structure, Quinoline -- Chemical properties, Biological sciences, Chemistry
Abstract

A new route is described for tetrahydroisoquinoline (THIQ) alkaloids involving the alkylation of [alpha]-aminonitrile as a key step, where the latter compound is prepared by anodic cyanation of the corresponding tertiary amine. The syntheses of ([plusmn])-carnegine, ([plusmn])-norlaudanosine and ([pulsmn])-O,O-dimethylcoclaurine are achieved.

Published
2010

15. Metal-free bronsted acid catalyzed formal [3 + 3] annulation: straightforward synthesis of dihydro-2H-chromenones, pyranones, and tetrahydroquinolinones

Author

Moreau, Julie, Hubert, Claudie, Batany, Jessika, Toupet, Loic, Roisnel, Thierry, Hurvois, Jean-Pierre, and Renaud, Jean-Luc

Subjects
Quinoline -- Chemical properties, Quinoline -- Structure, Ring formation (Chemistry) -- Usage, Biological sciences, Chemistry
Abstract

The application of the metal-free bronsted acid for the catalysis of the different addition reactions of numerous compounds is discussed. The process is shown to be extremely useful for the synthesis of the dihydro-2H-chromenones, and tetrahydroquinolinones under mild conditions.

Published
2009

19. Modified Fry Cyanation of a Chiral Pyridinium Salt: Asymmetric Syntheses of (-)-Coniine and (-)-Solenopsin A

Author

Vu, Van, Jouanno, Laurie-Anne, Cheignon, Adèle, Roisnel, Thierry, Dorcet, Vincent, Sinbandhit, Sourisak, Hurvois, Jean-Pierre, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Centre Régional de Mesures Physiques de l'Ouest (CRMPO), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES), Région Bretagne (BIPICAT project), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Rennes (UR)

Subjects
Alkaloids, Lithiation, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Total synthesis, Asymmetric synthesis, Chiral resolution
Abstract

International audience; The synthesis of chiral 2-cyano-Δ4-tetrahydropyridine 5 was carried out in 85 % yield through a modified two-step Fry reductive cyanation of pyridinium salt (+)-3c that used lithium triethylborohydride as the hydride donor. An alkylation-reduction sequence provided 2-alkyl-substituted tetrahydropyridines (+)-10a and (+)-10b in 72-75 % yield after chromatographic purification. This protocol has been applied to the asymmetric syntheses of piperidine alkaloids (-)-coniine and (-)-solenopsin A.

Published
2013
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