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Molecules 2013, 18(12), 14529-14542; doi:10.3390/molecules181214529
Article

Perfluoroalkanesulfonamide Organocatalysts for Asymmetric Conjugate Additions of Branched Aldehydes to Vinyl Sulfones

1, 2, 2, 2, 2, 2, 1, 1 and 1,*
1 Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan 2 Gifu Pharmaceutical University 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan
* Author to whom correspondence should be addressed.
Received: 30 October 2013 / Revised: 20 November 2013 / Accepted: 21 November 2013 / Published: 25 November 2013
(This article belongs to the Special Issue Dynamic Stereochemistry)
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Abstract

Asymmetric conjugate additions of branched aldehydes to vinyl sulfones promoted by sulfonamide organocatalyst 6 or 7 have been developed, allowing facile synthesis of the corresponding adducts with all-carbon quaternary stereocenters in excellent yields with up to 95% ee.
Keywords: organocatalyst; sulfonamide; vinyl sulfone; conjugate addition; quaternary stereocenters; fluorous organocatalyst; sulfonamide; vinyl sulfone; conjugate addition; quaternary stereocenters; fluorous
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Nakashima, K.; Murahashi, M.; Yuasa, H.; Ina, M.; Tada, N.; Itoh, A.; Hirashima, S.-I.; Koseki, Y.; Miura, T. Perfluoroalkanesulfonamide Organocatalysts for Asymmetric Conjugate Additions of Branched Aldehydes to Vinyl Sulfones. Molecules 2013, 18, 14529-14542.

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