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Wiley-VCH Verlag, ChemInform, 25(46), p. no-no, 2015

DOI: 10.1002/chin.201525039

Royal Society of Chemistry, Organic and Biomolecular Chemistry, 7(13), p. 2092-2099

DOI: 10.1039/c4ob02318h

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Asymmetric Syntheses of Three-Membered Heterocycles Using Chiral Amide-Based Ammonium Ylides

Journal article published in 2015 by Mathias Pichler, Johanna Novacek, Raphaël Robiette, Vanessa Poscher, Markus Himmelsbach ORCID, Uwe Monkowius, Norbert Mueller, Norbert Müller, Mario Waser ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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 compared to Evans or pseudoephedrine-based auxiliaries resulting in good to excellent stereoselectivities in both, epoxidation and aziridination reactions.