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Synfacts 2010(5): 0598-0598  
DOI: 10.1055/s-0029-1219743
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A Hydrogen Bonding Catalyzed Asymmetric Cascade to Tetrahydrocarbazoles

Contributor(s): Benjamin List, Steffen Müller
X.-F. Wang, J.-R. Chen, Y.-J. Cao, H.-G. Cheng, W.-J. Xiao*
Central China Normal University, Wuhan, P. R. of China
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

The authors report the hydrogenbonding catalyst 1 promoted catalytic asymmetric synthesis of tetrahydrocarbazoles from 2-pro­penylindoles and nitroolefins. The reaction is ­assumed to proceed via a Michael-Michael ­aromatization pathway rather than a concerted [4+2] cycloaddition. The described method uses a commercially available disulfonamide catalyst and gives rapid access to tetrahydrocarbazoles with three contiguous stereocenters in high yields and enantioselectivities.