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

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...

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Bibliographic Details
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
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Summary: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.

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