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The highly diastereoselective conjugate addition of lithium (S)-N-benzyl-N-(α-methylbenzyl)amide to a γ-silyloxy-α,β-unsaturated ester and in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine) and its C(2)-epimer. © 2007 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2007.10.026

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

22/10/2007

Volume

18

Pages

2510 - 2513