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Synfacts 2008(3): 0308-0308
DOI: 10.1055/s-2008-1042724
DOI: 10.1055/s-2008-1042724
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
NHC-Catalyzed Staudinger Reaction
Y.-R. Zhang, L. He, X. Wu, P.-L. Shao, S. Ye*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
Further Information
Publication History
Publication Date:
21 February 2008 (online)
Significance
A chiral N-heterocyclic carbene catalyzed Staudinger reaction of ketenes with N-Boc imines has been developed. Catalyst 1 in combination with Cs2CO3 has been found to be effective for this reaction. After investigating different N-protecting groups, N-Boc imines are found to be suitable for this reaction. With 10 mol% of triazolium salt 1, good to high yields (53-75%) and excellent enantioselectivities (er = 95:5 to >99:1) are obtained for a wide variety of ketenes and imines.