D. Chambers, G. Evans, A. Fairbanks
Jan 10, 2005
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Tetrahedron-asymmetry
Abstract
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 -Butyl esters are found to be unreactive to the Tebbe reagent, and as such tert -butyl protection may be used for other carboxylic acids.