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Synfacts 2006(10): 1064-1064
DOI: 10.1055/s-2006-949378
DOI: 10.1055/s-2006-949378
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
N-Heterocyclic Carbene-Catalyzed O- toC-Acyl Transfer
J. E. Thomson, K. Rix, A. D. Smith*
University of St. Andrews, UK
Further Information
Publication History
Publication Date:
21 September 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200610/lookinside/thumbnails/10.1055-s-2006-949378-1.jpg)
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.