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A Novel Method for the Asymmetric Synthesis of α , β ‐Diamino Acids by a Glucose‐Mediated Stereoselective Strecker Reaction
Author(s) -
Wang Dong,
Zhang PengFei,
Yu Biao
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790094
Subject(s) - chemistry , strecker amino acid synthesis , stereoselectivity , lewis acids and bases , chiral auxiliary , organic chemistry , stereochemistry , enantioselective synthesis , catalysis
A novel method for the asymmetric synthesis of α , β ‐diamino acids by using the 2,3,4,6‐tetra‐ O ‐pivaloyl‐ β ‐ D ‐glucopyranosyl group (Piv 4 Glc) as chiral auxiliary was developed ( Table and Scheme ). The reaction was promoted by CuBr⋅Me 2 S as Lewis acid, and high yields and good diastereoselectivities were achieved.