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Tandem conjugate addition of homochiral lithium N-benzyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS t Bu proceeds with high diastereoselectivity to give a homochiral anti-α-tert-butylthio-β-amino ester. Stepwise deprotection gives the corresponding free α-tert-butylthio-β-amino acid without epimerisation. Tandem conjugate addition of homochiral lithium N-allyl-N-(α-methylbenzyl)amide to tert-butyl cinnamate and enolate trapping with TsS t Bu followed by conversion of the S-tert-butyl group to a disulphide, and reduction with Lalancette's reagent generates polysubstituted thiomorpholine derivatives. © 2006 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2006.04.004

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

03/04/2006

Volume

17

Pages

1135 - 1145