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

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TETRAHEDRON-ASYMMETRY
卷 14, 期 8, 页码 1063-1072

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0957-4166(03)00073-9

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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) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.

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