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Synlett 2003(3): 0414-0416
DOI: 10.1055/s-2003-37119
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Effective Synthesis of α-Cyanoenamines by Peterson Olefination

Waldemar Adam, Claudio M. Ortega-Schulte*
Institute of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)8884756; e-Mail: adam@chemie.uni-wuerzburg.de;
Further Information

Publication History

Received 29 November 2002
Publication Date:
07 February 2003 (online)

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Abstract

A convenient and gentle method for the synthesis of α-cyanoenamines based on the Peterson olefination has been developed. For these sensitive, highly functionalized olefins, the present method is superior to the Horner-Emmons condensation, as manifested by the higher yields and broader scope.

Key words

α-Cyanoenamines - Peterson olefination - Horner-Emmons condensation

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5

In our preliminary attempts on the Peterson olefination, we have employed n-BuLi and LDA for the reaction with the aldehyde 2a, but obtained poor yields of the desired α cyanoenamine 3a, e.g., none with n-BuLi and only a 7% yield in the case of LDA.