Asymmetric conjugate addition of bromonitromethane to cyclic enones catalyzed by chiral monosulfonated diamines
摘要：
A series of chiral monosulfonated diamines were prepared and used as the catalysts for asymmetric conjugate addition of bromonitromethane to a,β-unsaturated ketones. The reaction provided nitrocyclopropanes in the presence of appropriate acid and base additives. 1,3,5-Triisopropylbenzenesulfonated 1,2-diphenylethane-1,2-diamine was found to be the best catalyst. The reaction of cyclohex-2-enone and cyclohept-2-enone gave the nitrocyclopropanes in excellent enantioselectivities and yields. Moderate enantioselectivities were obtained for cyclopent-2-enone. The hydrogen-bonding interaction between N-H bonds of sulfonamides and bromonitromethane is suggested to be important for the catalytic activity and enantioselectivity.
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关键词：
Asymmetric conjugate addition organocatalysis bromonitromethane alpha,beta-unsaturated ketone nitrocyclopropane
DOI：
10.3998/ark.5550190.0010.e18
被引量：
年份：
2009
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