Abstract
A new diamine catalyst has been developed for the asymmetric Michael reaction of cyclic ketones to nitroolefins. The catalyst is water-compatible and highly effective for the Michael reaction with nitroolefins when used in combination with TFA. With 10 mol% of catalyst 1 moderate to high diastereoselectivities (dr = 77:23 to 98:2) and enantioselectivities (er = 87:13 to 99.5:0.5) are obtained for different aromatic and heteroaromatic nitroolefins. A non-aromatic cyclohexyl nitroolefin has also been used with high enantioselectivity (er = 94:6).
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