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Qi Wu

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Name: 吴起; Wu, Qi
Organization: Zhejiang University , China
Department:
Title: Associate Professor(PhD)
Lipase/Acetamide-Catalyzed Carbon-Carbon Bond Formations: A Mechanistic View
Co-reporter:Xiao-Yang Chen;Guo-Jun Chen;Jun-Liang Wang;Xian-Fu Lin
Advanced Synthesis & Catalysis 2013 Volume 355( Issue 5) pp:864-868
Publication Date(Web):
DOI: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.

Stereoselective synthesis of spiro[5.5]undecane derivatives via biocatalytic [5+1] double Michael additions
Co-reporter:Xiao-Yang Chen, Yi-Ru Liang, Fang-Li Xu, Qi Wu, Xian-Fu Lin
Journal of Molecular Catalysis B: Enzymatic (15 December 2013) Volume 97() pp:18-22
Publication Date(Web):15 December 2013
DOI:10.1016/j.molcatb.2013.07.012
•A novel d-aminoacylase (DA)-catalyzed double Michael addition.•The specific catalytic effect of DA was demonstrated by control experiments.•Five spiro[5.5]undecane derivatives were prepared in moderate yield.•Only the cis isomers were obtained in all the cases.A novel enzymatic, promiscuous protocol of d-aminoacylase (DA)-catalyzed [5+1] double Michael addition was developed herein, for the synthesis of (hetero)spiro[5.5]undecane derivatives in moderate yields. It is notable that almost only the cis isomers were obtained through this biocatalytic methodology in all the cases according to their 1H and 13C NMR spectra. It is the first report on hydrolase-catalyzed double Michael addition in organic solvent.Download full-size image
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2-Butanone, 4-hydroxy-4-[4-(trifluoromethyl)phenyl]-, (4S)-
2-Butanone, 4-hydroxy-4-[4-(trifluoromethyl)phenyl]-, (4S)-
CAS:934548-93-3
2-Butanone, 4-hydroxy-4-[4-(trifluoromethyl)phenyl]-, (4S)-
Benzonitrile, 4-[(1S)-1-hydroxy-3-oxobutyl]-
Benzonitrile, 4-[(1S)-1-hydroxy-3-oxobutyl]-
CAS:934548-74-0
Benzonitrile, 4-[(1S)-1-hydroxy-3-oxobutyl]-
2-(aminomethyl)-3-(4-fluorophenyl)propanoic Acid
2-(aminomethyl)-3-(4-fluorophenyl)propanoic Acid
CAS:910443-83-3
2-(aminomethyl)-3-(4-fluorophenyl)propanoic Acid
1-Propanone, 3-hydroxy-1-phenyl-3-[4-(trifluoromethyl)phenyl]-
1-Propanone, 3-hydroxy-1-phenyl-3-[4-(trifluoromethyl)phenyl]-
CAS:874999-27-6
1-Propanone, 3-hydroxy-1-phenyl-3-[4-(trifluoromethyl)phenyl]-
TAK 285
TAK 285
CAS:871026-44-7
TAK 285
CYCLOHEXANONE, 2-[(4-FLUOROPHENYL)HYDROXYMETHYL]-
CYCLOHEXANONE, 2-[(4-FLUOROPHENYL)HYDROXYMETHYL]-
CAS:688802-13-3
CYCLOHEXANONE, 2-[(4-FLUOROPHENYL)HYDROXYMETHYL]-
3-Hexanone, 1-hydroxy-1-(4-nitrophenyl)-
3-Hexanone, 1-hydroxy-1-(4-nitrophenyl)-
CAS:673491-67-3
3-Hexanone, 1-hydroxy-1-(4-nitrophenyl)-
ACETAMIDE, 2-CYANO-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-
ACETAMIDE, 2-CYANO-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-
CAS:601487-94-9
ACETAMIDE, 2-CYANO-2-(1,2-DIHYDRO-2-OXO-3H-INDOL-3-YLIDENE)-
(R)-6-(4-((4-Ethylpiperazin-1-yl)methyl)phenyl)-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
(R)-6-(4-((4-Ethylpiperazin-1-yl)methyl)phenyl)-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine
CAS:497839-62-0
(R)-6-(4-((4-Ethylpiperazin-1-yl)methyl)phenyl)-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine