Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to d3-amino acids

Aitken, L. S., Hammond, L. E., Sundaram, R., Shankland, K. ORCID: https://orcid.org/0000-0001-6566-0155, Brown, G. D. and Cobb, A. J. A. (2015) Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to d3-amino acids. Chemical Communications, 51 (70). pp. 13558-13561. ISSN 1359-7345 doi: 10.1039/c5cc05158d

Abstract/Summary

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 d3-amino acids.

Item Type	Article
URI	https://reading-clone.eprints-hosting.org/id/eprint/41286
Item Type	Article
Refereed	Yes
Divisions	Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
Publisher	The Royal Society of Chemistry
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