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, Email: h-saitanabe.co.jp

H. Sai, T. Ogiku, H. Ohmizu, Synthesis, 2003, 201-204.

DOI: 10.1055/s-2003-36817

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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Key Words

α,β-dehydroamino acids, α,β-dehydropeptides, stereospecific, dehydration, syn-elimination, carbodiimide.

ID: J66-Y2003-1720

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

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