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A strategy for the asymmetric synthesis of homochiral [(R,R)- or (S,S)-], or meso-(R,S) bis-β-amino acid scaffolds, formally resulting from the stepwise conjugate addition of two differentially protected homochiral lithium amides to two α,β-unsaturated esters attached to a central arene, is demonstrated. Further manipulation enables the efficient synthesis of orthogonally protected pseudo-meso or pseudo-C2 symmetric scaffolds via selective N-benzyl or N-allyl deprotection, enabling regio-, stereo- and chemoselective functionalisation. © 2002 Elsevier Science Ltd. All rights reserved.

Original publication

DOI

10.1016/S0040-4020(02)00369-1

Type

Journal article

Journal

Tetrahedron

Publication Date

03/06/2002

Volume

58

Pages

4629 - 4642