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Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides.

Authors
Type
Published Article
Journal
Organic & Biomolecular Chemistry
1477-0539
Publisher
The Royal Society of Chemistry
Publication Date
Volume
13
Issue
7
Pages
2092–2099
Identifiers
DOI: 10.1039/c4ob02318h
PMID: 25521410
Source
Medline
License
Unknown

Abstract

The use of carbonyl-stabilised ammonium ylides to access chiral glycidic amides and the corresponding aziridines has so far been limited to racemic trans-selective protocols. We herein report the development of an asymmetric approach to access such compounds with high levels of stereoselectivity using easily accessible chiral auxiliary-based ammonium ylides. The use of phenylglycinol as the chiral auxiliary was found to be superior to Evans or pseudoephedrine-based auxiliaries resulting in good to excellent stereoselectivities in both, epoxidation and aziridination reactions.

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