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:
chatani
chem.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
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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
