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 |
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| Authors: | Otaka Akira Yukimasa Akira Watanabe Junko Sasaki Yoshikazu Oishi Sinya Tamamura Hirokazu Fujii Nobutaka |
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| Institution: | Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. aotaka@pharm.kyoto-u.ac.jp |
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| 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. |
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