Asymmetric aldol condensation in an ionic liquid-water system catalyzed by (S)-prolinamide derivatives

作者：Kucherenko A S^*; Syutkin D E; Zlotin S G

来源：Russian Chemical Bulletin, 2008, 57(3): 591-594.

DOI：10.1007/s11172-008-0092-x

• organocatalysis
• asymmetric aldol reaction
• ionic liquids
• water

Asymmetric aldol reaction of unmodified aldehydes with ketones catalyzed by 1(R),2(R)-bis(S)-prolinamido)cyclohexane (1) or (Rax)-2,2'-bis(( S)-prolinamido)-1,1'-binaphtyl (2) proceeds with high yield (68-99%) and diastereoselectivity (dr >= 75/25) in the system (1-butyl-3-methylimidazolium) tetrafluoroborate ([bmim][BF(4)])-water. The dependence of ee of the dominating anti-diastereomer of aldol on the percentage of water has a maximum at 50 vol.%. Catalyst 1 can be recycled 5 times without losses in the aldol yield, drand ee.

• 出版日期2008-3