Tetrahedron letters

Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2′, 6′-dimethyl-tyrosines

Y Han, S Liao, W Qiu, C Cai, VJ Hruby

Index: Han, Yinglin; Liao, Subo; Qiu, Wei; Cai, Chaozhong; Hruby, Victor J. Tetrahedron Letters, 1997 , vol. 38, # 29 p. 5135 - 5138

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Citation Number: 23

Abstract

All four stereoisomers of the highly constrained aromatic α-amino acid β-isopropyl-2′, 6′- dimethyltyrosine have been asymmetrically synthesized on a large scale. A catalytic asymmetric Michael addition of an organocuprate to a chiral α, β-unsaturated acyloxazolidinone and subsequent direct or indirect stereoselective electrophilic azidation of the α-position of the resulting product was followed by hydrolysis, hydrogenation and ...