二碘化钐（SmI₂）诱导的γ-乙酰氧基-α,β-烯酸酯还原反应与α-特异性动力学亲电捕获在氨基酸衍生物合成中的应用。

Application of samarium diiodide (SmI2)-induced reduction of gamma-acetoxy-alpha,beta-enoates with alpha-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives.

作者信息

Otaka Akira, Yukimasa Akira, Watanabe Junko, Sasaki Yoshikazu, Oishi Sinya, Tamamura Hirokazu, Fujii Nobutaka

机构信息

Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

出版信息

Chem Commun (Camb). 2003 Aug 7(15):1834-5. doi: 10.1039/b303718e.

DOI:10.1039/b303718e

PMID:12931990

Abstract

Gamma-acetoxy-alpha,beta-enoates were easily reduced by samarium diiodide (SmI2) in THF to generate samarium dienolates which were kinetically trapped with ease at their alpha-positions by electrophiles (proton, aldehydes or ketones) to yield (E)-alkene dipeptide isosteres or gamma-amino acid derivatives in high chemical yields.

摘要

γ-乙酰氧基-α,β-烯酸酯在四氢呋喃中很容易被二碘化钐（SmI₂）还原，生成二烯醇钐，该二烯醇钐在其α位很容易被亲电试剂（质子、醛或酮）动力学捕获，从而以高化学产率生成（E）-烯烃二肽类似物或γ-氨基酸衍生物。