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Issue 70, 2015
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Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ3-amino acids

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Abstract

An organocatalytic asymmetric synthesis of a novel, highly functionalised cyclopropane system furnished with versatile substituents and containing a quaternary centre is described. The process utilises a new bifunctional catalyst based on the cinchona alkaloid framework and the products made using this catalyst were obtained as single diastereoisomers, with very high enantioselectivities (up to 96% ee). We have also demonstrated that these resulting cyclopropanes are very useful synthetic intermediates to interesting products, such as the difficult to access δ3-amino acids.

Graphical abstract: Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ3-amino acids

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Supplementary files

Article information


Submitted
23 Jun 2015
Accepted
21 Jul 2015
First published
21 Jul 2015

This article is Open Access

Chem. Commun., 2015,51, 13558-13561
Article type
Communication
Author version available

Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ3-amino acids

L. S. Aitken, L. E. Hammond, R. Sundaram, K. Shankland, G. D. Brown and A. J. A. Cobb, Chem. Commun., 2015, 51, 13558
DOI: 10.1039/C5CC05158D

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