Lipase-catalyzed aza-Michael addition of amines to acrylates in supercritical carbon dioxide

被引：11

作者：

Zhang, Jiaxin ^{[1
]}

Wang, Ciduo ^{[1
]}

Wang, Chunyu ^{[2
]}

Shang, Wei ^{[1
]}

Xiao, Bao ^{[1
]}

Duan, Songhan ^{[1
]}

Li, Fengxi ^{[1
]}

Wang, Lei ^{[1
]}

Chen, Peng ^{[3
]}

机构：

[1] Jilin Univ, Sch Life Sci, Minist Educ, Key Lab Mol Enzymol & Engn, 2699 Qianjin St, Changchun 130023, Jilin, Peoples R China

[2] Jilin Univ, State Key Lab Supramol Struct & Mat, Changchun, Jilin, Peoples R China

[3] Second Hosp Jilin Univ, 218 Ziqiang St, Changchun 130022, Jilin, Peoples R China

来源：

JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY | 2019年 / 94卷 / 12期

关键词：

lipase; aza-Michael addition; supercritical; carbon dioxide; catalytic promiscuity; ENZYME PROMISCUITY; IONIC LIQUIDS; IMMOBILIZATION; EPOXIDATION; ACIDS;

D O I：

10.1002/jctb.6203

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

BACKGROUNDAza-Michael addition, a powerful method for the synthesis of beta -amino carbonyl derivatives, has been extensively studied in organic chemistry. In this study, the efficient and chemoselective aza-Michael addition of amines to acrylates catalyzed by lipase in supercritical carbon dioxide (scCO(2)) was reported for the first time. RESULTSUnder the optimal conditions [amine (1mmol), acrylate (1mmol), novozym 435 (20mg), 40 degrees C, scCO(2) (25mL, 10 MPa)], the corresponding Michael adducts of amines to acrylates were exclusively obtained in high yields (60-93%) for a short reaction time (1 h). No aminolysis was observed when scCO(2) was used as reaction medium. Moreover, novozym 435 showed high reusability in scCO(2) for aza-Michael addition. CONCLUSIONThe excellent chemoselectivity and reusability of novozym 435 in scCO(2) indicate the method's great potential for practical application. (c) 2019 Society of Chemical Industry

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页码：3981 / 3986

页数：6

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