Issue 23, 2012
From the journal:

Chemical Communications

Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile†

Michiko Sasaki,a   Tomo Takegawa,a   Hidaka Ikemoto,a   Masatoshi Kawahata,b   Kentaro Yamaguchib  and  Kei Takeda*a  

* Corresponding authors

a Department of Synthetic Organic Chemistry, Graduate School of Biomedical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-Ku, Hiroshima, Japan
E-mail: takedak@hiroshima-u.ac.jp
Fax: +81 82-257-5184
Tel: +81 82-257-5184

b Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa, Japan

Abstract

An α-chiral nitrile carbanion generated by deprotonation of enantioenriched O-carbamoyl cyanohydrin was trapped in situ with ethyl cyanoformate to give the corresponding ester derivative in 92% yield and 90 : 10 er, providing the first example of trapping of an α-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile.

Graphical abstract: Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile

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Article information

DOI
https://doi.org/10.1039/C2CC00082B
Article type
Communication
Submitted
05 Jan 2012
Accepted
27 Jan 2012
First published
30 Jan 2012

Chem. Commun., 2012,48, 2897-2899

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Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile

M. Sasaki, T. Takegawa, H. Ikemoto, M. Kawahata, K. Yamaguchi and K. Takeda, Chem. Commun., 2012, 48, 2897 DOI: 10.1039/C2CC00082B

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