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Asymmetric Conjugate Addition of Nitroalkanes to Enones Using a Sulfonamide-Thiourea Organocatalyst

Masahiro Kawada, Kosuke Nakashima, Shin-ichi Hirashima, Akihiro Yoshida, Yuji Koseki and Tsuyoshi Miura*

*Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan, Email: tmiuratoyaku.ac.jp

M. Kawada, K. Nakashima, S.-i. Hirashima, A. Yoshida, Y. Koseki, T. Miura, J. Org. Chem., 2017, 82, 6986-6991.

DOI: 10.1021/acs.joc.7b00835



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Abstract

The use of a sulfonamide-thiourea organocatalyst enables an asymmetric conjugate addition of nitroalkanes to α,β-unsaturated ketones to provide the corresponding γ-nitro carbonyl products in high yields with excellent enantioselectivities.

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Key Words

nitro compounds, 1,4-addition


ID: J42-Y2017