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The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide. © 2010 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2010.03.033

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

03/05/2010

Volume

21

Pages

1635 - 1648