Issue 20, 2011
From the journal:

Organic & Biomolecular Chemistry

Identification of the best-suited leaving group for the diastereoselective synthesis of glycidic amides from stabilised ammonium ylides and aldehydes†

Richard Herchl,a   Martin Stiftingerb  and  Mario Waser*a  

* Corresponding authors

a Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria
E-mail: Mario.waser@jku.at
Fax: +43 732 2468 8747
Tel: +43 732 2468 8748

b Institute of Analytical Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria

Abstract

In comparison to the use of sulfur ylides, the use of ammonium ylides for the synthesis of epoxides is significantly less developed. As a part of our systematic investigations concerning the use of amide-stabilised ammonium ylides for the synthesis of glycidic amides we have focused on the identification of the best-suited amino leaving group for this purpose. Whereas tertiary amines like quinuclidine or cinchona alkaloids were found to be not suited for epoxide formation, trimethylamine was found to be the leaving group of choice, yielding trans-glycidic amides in excellent yields of > 90%.

Graphical abstract: Identification of the best-suited leaving group for the diastereoselective synthesis of glycidic amides from stabilised ammonium ylides and aldehydes

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Article information

DOI
https://doi.org/10.1039/C1OB05721A
Article type
Paper
Submitted
06 May 2011
Accepted
24 Jun 2011
First published
11 Aug 2011
This article is Open Access

Org. Biomol. Chem., 2011,9, 7023-7027

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Identification of the best-suited leaving group for the diastereoselective synthesis of glycidic amides from stabilised ammonium ylides and aldehydes

R. Herchl, M. Stiftinger and M. Waser, Org. Biomol. Chem., 2011, 9, 7023 DOI: 10.1039/C1OB05721A

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