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Issue 7, 2015
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Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides

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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.

Graphical abstract: Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides

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Supplementary files

Article information


Submitted
31 Oct 2014
Accepted
01 Dec 2014
First published
01 Dec 2014

This article is Open Access

Org. Biomol. Chem., 2015,13, 2092-2099
Article type
Paper
Author version available

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

M. Pichler, J. Novacek, R. Robiette, V. Poscher, M. Himmelsbach, U. Monkowius, N. Müller and M. Waser, Org. Biomol. Chem., 2015, 13, 2092
DOI: 10.1039/C4OB02318H

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