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Synfacts 2007(7): 0737-0737
DOI: 10.1055/s-2007-968671
DOI: 10.1055/s-2007-968671
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Aziridination to Provide Aziridinyl Vinyl Ketones
Y. Deng, Y. R. Lee, C. A. Newman, W. D. Wulff*
Michigan State University, East Lansing, USA
Further Information
Publication History
Publication Date:
22 June 2007 (online)
Significance
The authors report the catalytic and asymmetric aziridination of vinyl diazoketones. High ee values and cis/trans ratios are obtained by using catalysts prepared from vapol or vanol ligand and triphenylborate. Moreover, this reaction seems to be highly tolerant of the substituents on the aryl imine employed. Lastly, the authors demonstrate that aziridinyl vinyl ketone 3 can be diastereoselectively reduced to the corresponding alcohol by choice of chelation- or non-chelation-controlled reducing conditions.