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

doi:10.1055/s-2003-36817

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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;

Abstract

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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.

Key words

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

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References

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

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