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Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/Z-Isomerization, Regioselectivity, and Synthetic Applications

Masaharu Sugiura*, Yasuhiko Ashikari, Yuka Takahashi, Koki Yamaguchi, Shunsuke Kotani, Makoto Nakajima

*Faculty of Pharmaceutical Sciences, Sojo University, 4-22-1 Ikeda, Nishi-ku, Kumamoto 860-0082, Japan, Email: msugiuraph.sojo-u.ac.jp

M. Sugiura, Y. Ashikari, Y. Takahashi, K. Yamaguchi, S. Kotani, M. Nakajima, J. Org. Chem., 2019, 84, 11458-11473.

DOI: 10.1021/acs.joc.9b01298 (free Supporting Information)


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Abstract

A chiral bisphosphine dioxide catalyzes an asymmetric conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane to provide saturated ketones with high enantioselectivities. Due to concomitant E/Z-isomerizations of enone substrates, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones.


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Key Words

1,4-reduction, organocatalysis, trichlorosilane


ID: J42-Y2019