Lipase/Acetamide‐Catalyzed Carbon‐Carbon Bond Formations: A Mechanistic View

• Published in: Advanced Synthesis & Catalysis
• Main Authors: Chen, Xiao‐Yang, Chen, Guo‐Jun, Wang, Jun‐Liang, Wu, Qi, Lin, Xian‐Fu
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2013
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/adsc.201201080; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.201201080; https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.201201080

Abstract A lipase B from Candida antarctica (CALB)/acetamide‐catalyzed Michael addition of less‐activated ketones and aromatic nitroolefins has been developed, which is particularly interesting because neither CALB nor acetamide can independently catalyze the reaction to any appreciable extent. This co‐catalyst system was applicable to the Michael additions of cyclic and acyclic ketones to a series of aromatic and heteroaromatic nitroolefins. Hydrogen bonds between acetamide and cyclohexanone were confirmed for the observed activation by experimental facts, and new mechanistic insights into CALB/acetamide co‐catalysis are presented.