Synthesis 2003(2): 0201-0204
DOI: 10.1055/s-2003-36817
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Syntheses of (E)-α,β-Dehydroamino Acids and (E)-α,β-De­hydropeptides by Stereospecific Dehydration with 1-Ethyl-3-(3-dimethyl­aminopropyl)carbodiimide (EDC)

Hiroshi Sai*, Tsuyoshi Ogiku, Hiroshi Ohmizu
Discovery Research Laboratory, Tanabe Seiyaku Co., Ltd. 3-16-89, Kashima, Yodogawa, Osaka 532-8505, Japan
Fax: +81(6)63002564; e-Mail: h-sai@tanabe.co.jp;
Further Information

Publication History

Received 10 September 2002
Publication Date:
22 January 2003 (online)

Abstract

Highly stereoselective syntheses of (E)-α,β-dehydroamino acids and (E)-α,β-dehydropeptides have been achieved in good yields by stereospecific dehydration of threo-β-hydroxy-α-amino acid derivatives using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) and CuCl2.

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In the case of CuCl similar result (90% yield, E:Z = 96:4) was obtained.