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Brønsted Acid Catalyzed Formal Insertion of Isocyanides into a C-O Bond of Acetals

Mamoru Tobisu, Aki Kitajima, Sachiko Yoshioka, Isao Hyodo, Masayuki Oshita and Naoto Chatani*

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan, Email: chatanichem.eng.osaka-u.ac.jp

M. Tobisu, A. Kitajima, S. Yoshioka, I. Hyodo, M. Oshita, N. Chatani, J. Am. Chem. Soc., 2007, 129, 11431-11437.

DOI: 10.1021/ja073286h (free Supporting Information)


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Abstract

The Brønsted acid catalyzed formal insertion of an isocyanide into a C-O bond of various acyclic and cyclic acetals can be applied to form α-alkoxy imidates. Functional groups, such as nitro, cyano, halogen, ester, and alkoxy groups, are tolerant to the reaction conditions employed. The course of the reaction is highly dependent on the structure of the isocyanide.

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Key Words

Carboxylic Acid Derivatives, Lactone Derivatives


ID: J48-Y2007-3120