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Synfacts 2010(7): 0800-0800
DOI: 10.1055/s-0029-1220087
DOI: 10.1055/s-0029-1220087
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Halogenated Quaternary Centers via Asymmetric Diels-Alder Reaction
K. Shibatomi*, K. Futatsugi, F. Kobayashi, S. Iwasa, H. Yamamoto*
Toyohashi University of Technology, Japan and the University of Chicago, USA
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Significance
The authors describe an enantioselective Diels-Alder reaction employing a Lewis acid activated chiral oxazaborolidine which was found to be a competent catalyst in previous studies (K. Futatsugi, H. Yamamoto Angew. Chem. Int. Ed. 2005, 44, 1484). Reaction of α-halogenated α,β-unsaturated ketones with dienes leads to the production of six-membered rings containing halogenated quaternary centers.