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Synfacts 2007(7): 0737-0737  
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

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
Y. Deng, Y. R. Lee, C. A. Newman, W. D. Wulff*
Michigan State University, East Lansing, USA
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Publikationsdatum:
22. Juni 2007 (online)

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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.