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Type: Artigo de periódico
Title: Stereoselective synthesis of the conformationally constrained glutamate analogue, (-)-(2R,3S)-cis-2-carboxyazetidine-3-acetic acid, from (S)-N-tosyl-2-phenylglycine
Author: Burtoloso, ACB
Correia, CRD
Abstract: The stereoselective synthesis of a novel cis conformationally constrained glutamate analogue containing an azetidine framework was accomplished from (S)-N-tosyl-2-phenylglycine in moderate overall yield. The key steps in the synthesis involved a N-H carbenoid insertion promoted by Cu(acaC)(2), a very efficient Wittig olefination of an azetidin-3-one, followed by a highly stereoselective rhodium-catalyzed hydrogenation. Epimerization of the cis to the trans analogue was performed using DBU as base in toluene at reflux.
Subject: azetidin-3-ones
glutamate analogues
N-H insertion
conformationally constrained amino acids
Wittig reaction
Country: Alemanha
Editor: Georg Thieme Verlag Kg
Rights: embargo
Identifier DOI: 10.1055/s-2005-869866
Date Issue: 2005
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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