Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael addition reactions of Aldehydes with Nitroolefins.

• Main Authors: Abdul Rahman, Mohd Basyaruddin, D. Headley, Allan, Dhungana, Kritanjali, M. Omar, Emmy
• Format: Article
• Language: English; English
• Published: Bentham Science Publishers 2011
• Online Access: http://psasir.upm.edu.my/id/eprint/25057/6/Ionic%20Liquid.pdf; http://psasir.upm.edu.my/id/eprint/25057/; http://www.benthamscience.com/
• Institution: Universiti Putra Malaysia

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.