Biocatalytic one-pot three-component synthesis of 3,3′-disubstituted oxindoles and spirooxindole pyrans using α-amylase from hog pancreas

被引：47

作者：

He, Tao ^{[1
]}

Zeng, Qing-Qing ^{[1
]}

Yang, Da-Cheng ^{[1
]}

He, Yan-Hong ^{[1
]}

Guan, Zhi ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

来源：

RSC ADVANCES | 2015年 / 5卷 / 47期

基金：

中国国家自然科学基金;

关键词：

CATALYZED MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; ENZYME PROMISCUITY; ALKALINE PROTEASE; NATURAL-PRODUCTS; LIPASE; CARBOHYDRATE; PROTEINASE; CONCISE;

D O I：

10.1039/c4ra16825a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

alpha-Amylase from hog pancreas displayed catalytic promiscuity in three-component reaction for the synthesis of 3,3'-disubstituted oxindoles and spirooxindole pyrans. The reactions between isatins, malononitrile and active methyl or active methylene compounds (acetone, nitromethane, indole, acetylacetone, 4-hydroxylcoumarin and dimedone) offered corresponding products via Knoevenagel/Michael reactions or Knoevenagel/Michael/cyclization reactions in one pot with high to excellent yields of up to 98% under mild reaction conditions. The alpha-amylase showed a broad spectrum of adaptability to various substrates. A possible mechanism of the alpha-amylase catalyzed three-component reaction was proposed.

引用

页码：37843 / 37852

页数：10

共 58 条

[1] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters [J].

Bencivenni, Giorgio ;

Wu, Li-Yuan ;

Mazzanti, Andrea ;

Giannichi, Berardino ;

Pesciaioli, Fabio ;

Song, Mao-Ping ;

Bartoli, Giuseppe ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) :7200-7203

[2] Catalytic promiscuity in biocatalysis: Using old enzymes to form new bonds and follow new pathways [J].

Bornscheuer, UT ;

Kazlauskas, RJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6032-6040

[3] 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

[4] Hydrolases in the Stereoselective Synthesis of N-Heterocyclic Amines and Amino Acid Derivatives [J].

Busto, Eduardo ;

Gotor-Fernandez, Vicente ;

Gotor, Vicente .

CHEMICAL REVIEWS, 2011, 111 (07) :3998-4035

[5] Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis [J].

Busto, Eduardo ;

Gotor-Fernandez, Vicente ;

Gotor, Vicente .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4504-4523

[6] The lipase-catalyzed asymmetric C-C Michael addition [J].

Cai, Jian-Feng ;

Guan, Zhi ;

He, Yan-Hong .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2011, 68 (3-4) :240-244

[7] One-Pot Synthesis of Spirooxindole Derivatives Catalyzed by Lipase in the Presence of Water [J].

Chai, She-Jie ;

Lai, Yi-Feng ;

Xu, Jiang-Cheng ;

Zheng, Hui ;

Zhu, Qing ;

Zhang, Peng-Fei .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :371-375

[8] Highly Enantioselective Construction of Spiro[4H-pyran-3,3′-oxindoles] Through a Domino Knoevenagel/Michael/Cyclization Sequence Catalyzed by Cupreine [J].

Chen, Wen-Bing ;

Wu, Zhi-Jun ;

Pei, Qing-Lan ;

Cun, Lin-Feng ;

Zhang, Xiao-Mei ;

Yuan, Wei-Cheng .

ORGANIC LETTERS, 2010, 12 (14) :3132-3135

[9] Trypsin-catalyzed direct asymmetric aldol reaction [J].

Chen, Yan-Li ;

Li, Wei ;

Liu, Yan ;

Guan, Zhi ;

He, Yan-Hong .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 87 :83-87

[10] Design, synthesis, and SAR of new pyrrole-oxindole progesterone receptor modulators leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (WAY-255348) [J].

Fensome, Andrew ;

Adams, William R. ;

Adams, Andrea L. ;

Berrodin, Tom J. ;

Cohen, Jeff ;

Huselton, Christine ;

Illenberger, Arthur ;

Kern, Jeffrey C. ;

Hudak, Valerie A. ;

Marella, Michael A. ;

Melenski, Edward G. ;

McComas, Casey C. ;

Mugford, Cheryl A. ;

Slayden, Ov D. ;

Yudt, Matthew ;

Zhang, Zhiming ;

Zhang, Puwen ;

Zhu, Yuan ;

Winneker, Richard C. ;

Wrobel, Jay E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (06) :1861-1873

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