Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes 英文参考文献.docVIP

Molecules 2010, 15, 2551-2563; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Organocatalytic Michael Addition of 1,3-Dicarbonyl Indane Compounds to Nitrostyrenes Zhen-Yu Jiang, Hua-Meng Yang, Ya-Dong Ju, Li Li, Meng-Xian Luo, Guo-Qiao Lai *, Jian-Xiong Jiang and Li-Wen Xu * Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China * Author to whom correspondence should be addressed: E-Mail: licpxulw@; Tel.: +86-571-288-67756; Fax: +86-571-288-65135. Received: 9 December 2009; in revised form: 3 March 2010 / Accepted: 19 March 2010 / Published: 12 April 2010 Abstract: To map out the efficient organocatalyst requirements in the Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes, a dozen different amino organocatalysts containing a p-toluenesulfonyl group (Ts) have been evaluated; excellent enantio- selectivities (up to er 92:8) were obtained with a primary amine-based Ts-DPEN catalyst and a plausible catalytic reaction mechanism was proposed on the basis of the experimental results. Keywords: organocatalysis, Michael reaction, primary amine, diamine 1. Introduction The addition of stabilized 1,3-dicarbonyl compounds to electro-deficient alkenes is one of the oldest and most useful key bond construction methods in organic synthesis for the formation of new C-C bonds [1]. Catalytic, enantioselective versions of this fundamental transformation which use metal- based chiral complex catalysts or organocatalysts have been reported extensively [2–8]. Early studies on organocatalytic asymmetric Michael reactions were conducted with readily available amines of natural origin, such as (-)-quinine and (+)-quinidine [9–11]. In the case of the Michael reaction of nitrostyrenes, the resulting 1,4-addition product is a very useful precursor to different