Synthesis of enantiopure (R, R)-and (S, S)-cis-2, 3-propanoprolines

NA Kopylova, OO Grygorenko, IV Komarov…

Index: Kopylova, Natalia A.; Grygorenko, Oleksandr O.; Komarov, Igor V.; Groth, Ulrich Tetrahedron Asymmetry, 2010 , vol. 21, # 23 p. 2868 - 2871

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Citation Number: 7

Abstract

A novel approach to the synthesis of an enantiopure bicyclic proline analogue, hexahydrocyclopenta [b] pyrrole-6a (1H)-carboxylic acid ('2, 3-propanoproline'), has been developed. The method relied on tandem Strecker-nucleophilic cyclization reaction of 2-(2- bromoethyl) cyclopentanone. The overall synthetic scheme included six steps and resulted in 18% overall yield of both enantiomers of the title amino acid.