Tetrahedron: Asymmetry

First synthesis of (1S, 2S)-and (1R, 2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones

M Truong, F Lecornué, A Fadel

Index: Truong, Molika; Lecornue, Frederic; Fadel, Antoine Tetrahedron Asymmetry, 2003 , vol. 14, # 8 p. 1063 - 1072

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Citation Number: 37

Abstract

An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) ...