Download PDF
Synfacts 2010(7): 0800-0800  
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

Contributor(s): Mark Lautens, David A. Candito
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)

    Permissions and Reprints

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.