1307904-03-5Relevant articles and documents
Diphenylprolinol silyl ether-derived thioureas as highly efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes
He, Chunyan,Ren, Xiaochen,Feng, Yingle,Chai, Yonghai,Zhang, Shengyong,Chen, Weiping
, p. 4036 - 4038 (2015)
Abstract This Letter described the synthesis of the first diarylprolinol silyl ether-derived bifunctional thiourea organocatalysts. The catalysts were applied to the asymmetric Michael addition of aldehydes to nitroalkenes to give the desired adducts in good yields (up to 99%) with excellent enantioselectivities (up to 99% ee) and excellent diastereoselectivities (up to 99:1). The spatial placement of C-4 substituent is of importance to the reaction activity and stereoselectivity.
Ionic liquid-supported (ILS) (S)-pyrrolidine sulfonamide for asymmetric Michael addition reactions of aldehydes with nitroolefins
Omar, Emmy M.,Dhungana, Kritanjali,Headley, Allan D.,Rahman, Mohd Basyaruddin Abdul
experimental part, p. 170 - 175 (2012/04/05)
A class of ionic liquid supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst (1c), which was developed earlier in our lab, has been applied to a wider range of Michael addition reaction, involving various aryl-substituted nitroolefins and a series of aldehydes. Catalyst 1c catalyzes Michael additions in which only 2 equivalents of aldehydes to each equivalent of nitroolefin are required. With 10 mol% of ILS catalyst 1c loading, moderate to excellent yields (51-98%) with moderate enantioselectivities (28-83% ee) and high diastereoselectivities (syn/anti ratio up to 97/3) were obtained. Moreover, the catalyst 1c could be easily recycled and reused for at least 5 times with slightly reduced activities.