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

By William J. Nodes, Kenneth Shankland, Sundaram Rajkumar and Alexander John Andre Cobb

Abstract

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

Publisher: Thieme Publishing
Year: 2010
OAI identifier: oai:centaur.reading.ac.uk:16160

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