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237 results on '"Tenaglia, Alphonse"'

1. Indium-catalysed ring opening of 2-hydroxybutyrolactone through the cleavage of C(sp$^3$)–O bond

Author

Aoun, Sameh, Massouh, Joe, Scornet, Noémie, Giordano, Laurent, Tenaglia, Alphonse, Buono, Gérard, Rey, Patrick, Bellière-Baca, Virginie, and Hérault, Damien

Subjects
Methionine, Lactone, Sulfur nucleophiles, Indium, Thiol, Biochemistry, QD415-436, Physical and theoretical chemistry, QD450-801, Mathematics, QA1-939
Abstract

The ring opening by the cleavage of the C(sp$^3$)–O bond of 2-hydroxybutyrolactone with (ethylthio)trimethylsilane was effectively catalysed by indium triiodide. Screening the reaction conditions allowed optimizing the ring opening. The effect of the nucleophile/catalyst ratio on the reaction efficiency has also been demonstrated. After optimization, 2-hydroxy-4-(ethylthio)butyric acid was isolated with an excellent yield (85%), thus making this method useful for the preparation of methionine analogues.

Published
2023
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4. CpRuCl(PPh3)(sub 2)-catalyzed cyclopropanation of bicyclic alkenes with tertiary propargylic acetates

Author

Tenaglia, Alphonse and Marc, Sylvain

Subjects
Cyclopentadiene -- Atomic properties, Ruthenium -- Atomic properties, Olefins -- Atomic properties, Acetates -- Atomic properties, Biological sciences, Chemistry
Abstract

The electron-rich cyclopentadienylruthenium complex CpRuCl(PPh3)(sub 2) has turned out to be an efficient catalyst for the cyclopropanation of a wide range of norbornenes and norbornadienes with propargylic carboxylates. An efficient cyclopropanation of cyclobutenes is demonstrated, providing the strained bicyclo[2.1.0(super 1,3)]pentane framework.

Published
2006

5. Cobalt(I)-catalyzed [6+2] cycloadditions of cyclooctatetra(tri)ene with alkynes

Author

Achard, Mathieu, Mosrin, Marc, Tenaglia, Alphonse, and Buono, Gerard

Subjects
Ring formation (Chemistry) -- Analysis, Tautomers -- Chemical properties, Biological sciences, Chemistry
Abstract

A [6+2] cycloaddition of cycloheptatriene (CHT) with terminal alkynes catalyzed by Co(I) complexes to afford bicyclo[4.2.1]trienes is reported. The reactions with 1,3,5-cyclooctatriene (COT) give both [6+2] and [4+2] adducts as a result of the valence tautomerism of COT.

Published
2006

6. A straightforward route to stereodefined functionalized cycloheptanols and cyclooctanols

Author

Buono, Frederic and Tenaglia, Alphonse

Subjects
Organic compounds -- Synthesis, Natural products -- Research, Condensation products (Chemistry) -- Research, Biological sciences, Chemistry
Abstract

A four-step diastereoselective approach to convert cyclopentanones into functionalized cycloheptanols is described. The transformation occurs via a palladium-catalyzed bicycloannulation of cycloalkanones with Baeyer-Villiger oxidation followed by bi- and polycyclic lactone reductive ring opening.

Published
2000

7. Regio- and stereoselective functionalization of deltacyclenes: a route to the synthesis of optically active (+)-deltacyclan-8-one

Author

Tenaglia, Alphonse, Pardigon, Olivier, and Buono, Gerard

Subjects
Cyclic compounds -- Research, Organic compounds -- Synthesis, Biological sciences, Chemistry
Abstract

The synthesis and characterization of optically active (+)-deltacyclan-8-one are described. The scheme involves the direct and stereocontrolled functionalization of 8-substituted deltacyclenes by electrophilic activation to form the 8,9- or 5,8-difunctionalized deltacyclenes. The reaction conditions and mechanism for the synthesis are presented.

Published
1996

8. Enantioselective syntheses of monofunctionalized deltacyclenes using a (CoI2/Zn) catalytic system

Author

Pardigon, Olivier, Tenaglia, Alphonse, and Buono, Gerard

Subjects
Cyclic compounds -- Research, Biological sciences, Chemistry
Abstract

The homo Diels-Alder (HDA) reaction is extended to 2-propyn-1-ol(propargyl alcohol) and 3-butyn-1-ol to generate two different classes of compounds. The HDA is widely used for the synthesis of tetracyclic compounds called Deltacyclenes originating from acetylenic and norbornadiene compounds. The extension is acheived by the stereochemical control of the parent compounds. The deltacyclenes that are potential precursors of tricyclic functionalized compounds and deltacyclenes with an allylic acetate functionality are the two different groups of compounds produced.

Published
1995

13. Highly regio- and stereocontrolled formation of functionalized tricycle [4.2.1.[0.sup.2,8]]non-3-enes

Author

Toselli, Nicolas, Martin, David, Achard, Mathieu, Tenaglia, Alphonse, and Buono, Gerard

Subjects
Isopropanol -- Chemical properties, Isopropanol -- Structure, Benzoic acid -- Structure, Benzoic acid -- Chemical properties, Ring-opening polymerization -- Analysis, Biological sciences, Chemistry
Abstract

The electrophilic activations of bicycle[4.2.1]nonatrienes by 4-isopropyl-1,2,4-triazolinedione, N-iodosuccinimide, or epoxidation/acidic ring-opening sequence is described. The in situ trappings by water, alcohols or benzoic acids has led to the original tricycle[4.2.1.[0.sup.2,8]]non-3-enes with high regio- and stereoselectivities.

Published
2009

14. Ruthenium-catalyzed cross-coupling of 7-azabenzonorbornadienes with alkynes. An entry to 3a,9b-dihydrobenzo[g]indoles

Author

Tenaglia, Alphonse and Marc, Sylvain

Subjects
Ring formation (Chemistry) -- Analysis, Ruthenium -- Structure, Ruthenium -- Chemical properties, Spin coupling -- Research, Biological sciences, Chemistry
Abstract

Electron-rich half-sandwich ruthenium complex CpRuI[(P[Ph.sub.3]).sub.2] has catalyzed the coupling reaction of 7-azabenzonorbornadienes with alkynes to form 3a,9b-dihydrobenzo[g]indoles. The scope and limitations of the reaction are discussed according to the substitution patterns of the alkyne and of the substituent at the nitrogen atom of the azabenzonorbornadiene.

Published
2008

24. Ruthenium-Catalyzed [2+2+2] Cycloaddition of 1,6-Enynes and Unactivated Alkynes: Access to Ring-Fused Cyclohexadienes.

Author

Liu, Rui, Giordano, Laurent, and Tenaglia, Alphonse

Subjects
RUTHENIUM catalysts, RING formation (Chemistry), ALKYNES, CYCLOHEXADIENE, REGIOSELECTIVITY (Chemistry)
Abstract

The [2+2+2] intermolecular carbocyclization reactions between 1,6-enynes and alkynes catalyzed by [RuCl(cod)(Cp*)] (cod=1,5-cyclooctadiene, Cp*=pentamethylcyclopentadienyl) are reported to provide bicyclohexa-1,3-dienes. The presented reaction conditions are compatible with internal and terminal alkynes and the chemo- and regioselectivity issues are controlled by the presence of substituents at the propargyl carbon center of the alkyne(s) partner(s). [ABSTRACT FROM AUTHOR]

Published
2017
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