New Chemistry with Old Functional Groups: On the Reaction of Isonitriles with Carboxylic Acids—A Route to Various Amide Types

Xuechen Li† and Samuel J. Danishefsky†‡
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, and Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027
J. Am. Chem. Soc., 2008, 130 (16), pp 5446–5448
DOI: 10.1021/ja800612r
Publication Date (Web): March 28, 2008
Copyright © 2008 American Chemical Society
†

Sloan-Kettering Institute for Cancer Research.

,
‡

Columbia University.

Abstract

Abstract Image

Thermolysis of isonitriles with carboxylic acids provides, in one step, N-formyl imides (see, for example, 8 + 19 → 21). The resultant N-formyl group can be converted to N−H, NCH2OH, or NCH3. This chemistry allows for a new route for synthesizing β-N (asparagine)-linked glycosyl amino acids.

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History

  • Published In Issue April 23, 2008
  • Article ASAPMarch 28, 2008
  • Received: January 25, 2008

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