LeHavreV1, France, Analysis, bibRecord, 000B18

Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.

Identifieur interne : 000B18 ( France/Analysis ); précédent : 000B17; suivant : 000B19

Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.

Auteurs : Frédéric Pin [France] ; Sébastien Comesse ; Bernard Garrigues ; Stefan Marchalín ; Adam Daïch

Source :

The Journal of organic chemistry [ 0022-3263 ] ; 2007.

RBID : pubmed:17243717

Abstract

Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).

DOI: 10.1021/jo062077x
PubMed: 17243717

Affiliations:

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pubmed:17243717

Le document en format XML

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<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
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<front><div type="abstract" xml:lang="en">Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).</div>
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Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.

Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.

Source :

Abstract

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Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki

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