Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C-C bond formation in a "one-pot" synthesis

被引：167

作者：

Li, Kun ^{[1
]}

He, Ting ^{[1
]}

Li, Chao ^{[1
]}

Feng, Xing-Wen ^{[1
]}

Wang, Na ^{[1
]}

Yu, Xiao-Qi ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

GREEN CHEMISTRY | 2009年 / 11卷 / 06期

基金：

中国国家自然科学基金;

关键词：

SURFACTANT-COMBINED CATALYST; MARKOVNIKOV ADDITION; ASYMMETRIC-SYNTHESIS; BETA-AMINO; EVOLUTIONARY; ALDEHYDES;

D O I：

10.1039/b817524a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel lipase-catalysed direct Mannich reaction has been developed under aqueous conditions in a "one-pot" strategy. Interestingly, these promiscuous reactions can be greatly promoted by water and generally require aromatic aldehydes.

引用

页码：777 / 779

页数：3

共 38 条

[1] HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system [J].

Akiyama, T ;

Matsuda, K ;

Fuchibe, K .

SYNLETT, 2005, (02) :322-324

[2]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[3]

2-E

[4] Strategies for altering enzyme reaction specificity for applied biocatalysis [J].

Berglund, P ;

Park, S .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (04) :325-336

[5] Water in organocatalytic processes: Debunking the myths [J].

Blackmond, Donna G. ;

Armstrong, Alan ;

Coombe, Vyv ;

Wells, Andrew .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (21) :3798-3800

[6] Aldol additions with mutant lipase: analysis by experiments and theoretical calculations [J].

Branneby, C ;

Carlqvist, P ;

Hult, K ;

Brinck, T ;

Berglund, P .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 31 (4-6) :123-128

[7] Carbon-carbon bonds by hydrolytic enzymes [J].

Branneby, C ;

Carlqvist, P ;

Magnusson, A ;

Hult, K ;

Brinck, T ;

Berglund, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (04) :874-875

[8] Exploring the active-site of a rationally redesigned lipase for catalysis of Michael-type additions [J].

Carlqvist, P ;

Svedendahl, M ;

Branneby, C ;

Hult, K ;

Brinck, T ;

Berglund, P .

CHEMBIOCHEM, 2005, 6 (02) :331-336

[9] Chiral Bronsted acid-catalyzed direct asymmetric Mannich reaction [J].

Guo, Qi-Xiang ;

Liu, Hua ;

Guo, Chang ;

Luo, Shi-Wei ;

Gu, Yi ;

Gong, Liu-Zhu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) :3790-+

[10] Catalytic promiscuity of halohydrin dehalogenase and its application in enantioselective epoxide ring opening [J].

Hasnaoui-Dijoux, Ghannia ;

Elenkov, Maja Majeric ;

Spelberg, Jeffrey H. Lutje ;

Hauer, Bernhard ;

Janssen, Dick B. .

CHEMBIOCHEM, 2008, 9 (07) :1048-1051

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