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Catalytic Activity of epi-Quinine-Derived 3,5-Bis(trifluoromethyl)benzamide in Asymmetric Nitro-Michael Reaction of Furanones.

Research paper by Tohru T Sekikawa, Takayuki T Kitaguchi, Hayato H Kitaura, Tatsuya T Minami, Yasuo Y Hatanaka

Indexed on: 13 Jun '15Published on: 13 Jun '15Published in: Organic Letters



Abstract

High catalytic activity of novel epi-quinine-derived 3,5-bis(CF3)benzamide in the asymmetric nitro-Michael reaction is described. With 0.1-5 mol % loadings of this catalyst, the addition of 5-substituted 2(3-H)-furanones to a wide range of nitroalkenes involving challenging substrates, β-alkylnitroalkenes, smoothly proceeded, giving the Michael adducts in high yields (>90%) with excellent diastereo- and enantioselectivity (>98:2 dr, syn major; 88-98% ee). DFT calculation was carried out to account for the high catalytic activity.