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Synfacts 2006(10): 1064-1064  
DOI: 10.1055/s-2006-949378
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

N-Heterocyclic Carbene-Catalyzed O- toC-Acyl Transfer

Contributor(s): Benjamin List, Subhas Chandra Pan
J. E. Thomson, K. Rix, A. D. Smith*
University of St. Andrews, UK
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

Here the authors report an efficient N-heterocyclic carbene catalyzed O- to C-acyl transfer of different amino acid derived O-acyl alkyl or aryl carbonates. The triazolium salt 1 in combination with KHMDS has been found to be effective for this reaction. With 1-5 mol% of the catalyst different amino acid derived O-acyl alkyl or aryl carbonates have been rearranged to their corresponding C-acyl azalactones with 67-84% yield.