Elsevier

Tetrahedron Letters

Volume 52, Issue 17, 27 April 2011, Pages 2209-2211
Tetrahedron Letters

A practical and inexpensive ‘convertible’ isonitrile for use in multicomponent reactions

This Letter is dedicated to our dear friend and colleague, Harry H. Wasserman, in honor of his many years of service to Tetrahedron Publications and on the occasion of his 90th birthday
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Abstract

N-tert-Butylamides are readily converted into the corresponding carboxylic acids by simple nitrosation. The process, which occurs under mild nonaqueous conditions, leaves carboxylic esters untouched and transforms multicomponent reaction products into useful building blocks for further synthetic elaboration.

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Acknowledgments

The authors thank Messrs. Henry Kaweesi and Alexei Aidan for helpful experimental assistance. Support of the Cornell NMR Facility has been provided by NSF (CHE 7904825; PGM 8018643) and NIH (RR02002).

References and notes (14)

  • M.A. Mironov

    QSAR Comb. Sci.

    (2006)
  • E.H. White

    J. Am. Chem. Soc.

    (1955)
    E.H. White

    J. Am. Chem. Soc.

    (1955)
  • C. Hulme et al.

    Curr. Med. Chem.

    (2003)
    A. Dömling

    Curr. Opin. Chem. Biol.

    (2000)
  • N. Elders et al.

    Angew. Chem., Int. Ed.

    (2009)
  • A. Dömling

    Chem. Rev.

    (2006)
    A. Dömling et al.

    Angew. Chem., Int. Ed.

    (2000)
  • T.A. Keating et al.

    J. Am. Chem. Soc.

    (1995)
  • T. Lindhorst et al.

    Tetrahedron

    (1999)
There are more references available in the full text version of this article.

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