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Asymmetric phase-transfer-catalyzed synthesis of five-membered cyclic gamma-Amino acid precursors

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Nodes, W. J., Shankland, K., Rajkumar, S. and Cobb, A. J. A. (2010) Asymmetric phase-transfer-catalyzed synthesis of five-membered cyclic gamma-Amino acid precursors. Synlett , 2010 (20). pp. 3011-3014. ISSN 1437-2096

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To link to this article DOI: 10.1055/s-0030-1259050

Abstract/Summary

The first example of an intramolecular enantioselective Michael addition of nitronates onto conjugated systems utilizing a chiral phase-transfer catalyst is described. A range of five-membered gamma-nitro esters with up to three stereocentres have been prepared and the relative and absolute configurations proven by chemical and crystallographic methods. The products are rapidly obtained and are precursors to five-membered cyclic gamma-amino acids.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Medicinal Chemistry Research Group
ID Code:16160
Uncontrolled Keywords:organocatalysis, phase transfer, intramolecular, nitronate, Michael addition
Publisher:Thieme Publishing

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