PAPER	Synthesis 2006: 2649-2652   DOI: 10.1055/s-2006-942483
© Georg Thieme Verlag Stuttgart · New York
Construction of Tetrasubstituted Carbon by an Organocatalyst: Cyanation Reaction of Ketones and Ketimines Catalyzed by a Nucleophilic N-Heterocyclic Carbene
Yoshimasa Fukuda, Kazuhiro Kondo*, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan Fax: +81(52)8363439; e-Mail: kazuk@phar.nagoya-cu.ac.jp; e-Mail: aoyama@phar.nagoya-cu.ac.jp;
Received 10 March 2006

Abstract

A method for cyanation reaction of ketones and ketimines having lower reactivity than aldehydes and aldimines with TMSCN in the presence of N-heterocyclic carbene prepared from 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride and potassium tert-butoxide, as a nucleophilic organocatalyst, is described. These cyanations of ketones and ketimines afford the corresponding products in good yields under mild reaction conditions.

Keywords

N-heterocyclic carbene - tetrasubstituted carbon - nucleophilic organocatalyst - cyanation - trimethylsilyl cyanide