Issue 15, 2003
From the journal:

Chemical Communications

Application of samarium diiodide (SmI2)-induced reduction of γ-acetoxy-α,β-enoates with α-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives

Akira Otaka,*a   Akira Yukimasa,a   Junko Watanabe,a   Yoshikazu Sasaki,a   Sinya Oishi,a   Hirokazu Tamamuraa  and  Nobutaka Fujiia  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan
E-mail: aotaka@pharm.kyoto-u.ac.jp
Fax: +81-75-753-4570
Tel: +81-75-753-4571

Abstract

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

Graphical abstract: Application of samarium diiodide (SmI2)-induced reduction of γ-acetoxy-α,β-enoates with α-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives

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Article information

DOI
https://doi.org/10.1039/B303718E
Article type
Communication
Submitted
04 Apr 2003
Accepted
28 May 2003
First published
18 Jun 2003

Chem. Commun., 2003, 1834-1835

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Application of samarium diiodide (SmI2)-induced reduction of γ-acetoxy-α,β-enoates with α-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives

A. Otaka, A. Yukimasa, J. Watanabe, Y. Sasaki, S. Oishi, H. Tamamura and N. Fujii, Chem. Commun., 2003, 1834 DOI: 10.1039/B303718E

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