Tetrahedron

Synthesis of enantiomerically enriched β, γ-unsaturated-α-amino acids

NGW Rose, MA Blaskovich, A Wong, GA Lajoie

文献索引：Rose, Nicholas G.W; Blaskovich, Mark A; Wong, Alex; Lajoie, Gilles A Tetrahedron, 2001 , vol. 57, # 8 p. 1497 - 1507

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被引用次数: 28

摘要

A variety of enantiomerically enriched β, γ-unsaturated-α-amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70–95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains ...