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Lipase/Acetamide‐Catalyzed Carbon‐Carbon Bond Formations: A Mechanistic View
Author(s) -
Chen XiaoYang,
Chen GuoJun,
Wang JunLiang,
Wu Qi,
Lin XianFu
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201201080
Subject(s) - acetamide , candida antarctica , chemistry , cyclohexanone , catalysis , organic chemistry , lipase , hydrogen bond , candida tropicalis , yeast , enzyme , molecule , biochemistry
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.