Tetrahedron: Asymmetry

Synthesis of C-glycosyl amino acids: scope and limitations of the tandem Tebbe/Claisen approach

DJ Chambers, GR Evans, AJ Fairbanks

Index: Chambers, David J.; Evans, Graham R.; Fairbanks, Antony J. Tetrahedron Asymmetry, 2005 , vol. 16, # 1 p. 45 - 55

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Citation Number: 42

Abstract

Amino acids may be used as coupling partners for esterification with 3-hydroxy glycals as substrates for the tandem Tebbe/Claisen approach to the synthesis of C-glycosyl amino acids. Whilst esters of substituted α-amino acids do not successfully undergo Tebbe, or other, methylenation, esters of β-or γ-amino acids are methylenated to yield vinyl ethers, which then undergo smooth thermal rearrangement to yield β-C-glycoside products. tert- ...