通过双功能硫脲基催化的硝基甲烷与二烯酮的双重迈克尔加成反应，高效合成光学活性 4-硝基环己酮。
Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones.
机构信息
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
出版信息
Chem Commun (Camb). 2011 Apr 7;47(13):3992-4. doi: 10.1039/c0cc05418f. Epub 2011 Feb 17.
PMID:21331389
Abstract
Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).
摘要
硫脲改性金鸡纳生物碱作为双功能催化剂和碱，可以催化二乙烯基酮与硝基甲烷的分步[5+1]环化反应，通过双重迈克尔加成反应，以良好的收率、优异的非对映选择性（>20:1）和高对映体过量值（高达 97:3）得到光学活性的 4-硝基环己酮。
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