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Synlett 2005(6): 0892-0899  
DOI: 10.1055/s-2005-864831
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Racemic Tertiary Cyanohydrins

Fu-Xue Chen, Xiaoming Feng*
Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Fax: +86(28)85418249; e-Mail: xmfeng@scu.edu.cn;
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Publication History

Received 6 December 2004
Publication Date:
23 March 2005 (online)

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Abstract

The addition of TMS-CN to ketones is catalyzed by ­homo- and heterogeneous catalysts, which are rationally designed by the line of hydrogen bond activation, dual activation, and the general concept of green chemistry. Especially noteworthy is that those approaches could be readily transferred to enantioselective version of the art. This account describes the development of the catalyst and comparison of the catalytic capacity depending on the nature of the catalyst and structural modifications with mechanism elucidation in appropriate position.

1 Introduction

2 Through Homogeneous Catalysis

2.1 With Lewis Acids

2.2 With Organocatalysts

2.3 With Dual Activation Catalysts

2.3.1 With Bifunctional Catalysts

2.3.2 With Double-Activation Catalysts

3 Through Heterogeneous Catalysis

3.1 Prior Art

3.2 With Inorganic and Organic Salts

4 Summary and Perspectives

Key words

alcohols - catalysis - ketones - nitriles - nucleophilic additions