Synthesis of dihydropyrano[4,3-b]pyranes via a multi-component reaction catalyzed by lipase

被引：15

作者：

Chen, Xiao ^{[1
]}

Zhang, Weian ^{[1
]}

Yang, Fengjuan ^{[1
]}

Guo, Chao ^{[1
]}

Zhao, Ziyuan ^{[1
]}

Ji, Di ^{[3
]}

Zhou, Fan ^{[1
]}

Wang, Zhi ^{[1
]}

Zhaob, Rui ^{[2
]}

Wang, Lei ^{[1
]}

机构：

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

[2] Jilin Univ, China Japan Union Hosp, Changchun, Peoples R China

[3] First Middle Sch Changchun City, Changchun, Peoples R China

来源：

GREEN CHEMISTRY LETTERS AND REVIEWS | 2017年 / 10卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Lipase; promiscuity; multi-component reaction; dihydropyrano[4,3-b]pyranes; AQUEOUS-MEDIA; 2-AMINO-2-CHROMENES; DERIVATIVES; WATER;

D O I：

10.1080/17518253.2017.1285442

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A green method for the synthesis of dihydropyrano[4,3-b]pyranes via a three-component reaction catalyzed by lipase is reported firstly. Under the optimal conditions, high yields of dihydropyrano [4,3-b] pyranes (80.8-96.8%) could be obtained in this enzymatic reaction. This study not only expands the application of lipase in organic synthesis, but also provides an alternative efficient method for the synthesis of dihydropyrano[4,3-b]pyranes. [GRAPHICS] .

引用

页码：54 / 58

页数：5

共 30 条

[1] Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media
Ballini, R
Bosica, G
Conforti, ML
Maggi, R
Mazzacani, A
Righi, P
Sartori, G
[J]. TETRAHEDRON, 2001, 57 (07) : 1395 - 1398
[2] The remarkable catalytic activity of ultra-small free-CeO2 nanoparticles in selective carbon-carbon bond formation reactions in water at room temperature
Banerjee, Subhash
[J]. NEW JOURNAL OF CHEMISTRY, 2015, 39 (07) : 5350 - 5353
[3] Remarkable catalytic activity of silica nanoparticle in the bis-Michael addition of active methylene compounds to conjugated alkenes
Banerjee, Subhash
Santra, Swadeshmukul
[J]. TETRAHEDRON LETTERS, 2009, 50 (18) : 2037 - 2040
[4] PPL catalyzed four-component PASE synthesis of 5-monosubstituted barbiturates: Structure and pharmacological properties
Bihani, Manisha
Bora, Pranjal P.
Verma, Alakesh K.
Baruah, Reshita
Boruah, Hari Prasanna Deka
Bez, Ghanashyam
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (24) : 5732 - 5736
[5] Beyond enzymatic promiscuity: asymmetric induction by L-proline on lipase catalyzed synthesis of polyfunctionalized 4H-pyrans
Bora, Pranjal P.
Bihani, Manisha
Bez, Ghanashyam
[J]. RSC ADVANCES, 2015, 5 (62) : 50597 - 50603
[6] Multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles catalyzed by lipase from Aspergillus niger
Bora, Pranjal P.
Bihani, Manisha
Bez, Ghanashyam
[J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 92 : 24 - 33
[7] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[8] 2-U
[9] Jin T. S., 2003, SYN LETT, V35, P2001
[10] Model Studies on the First Enzyme-Catalyzed Ugi Reaction
Klossowski, Szymon
Wiraszka, Barbara
Berlozecki, Stanislaw
Ostaszewski, Ryszard
[J]. ORGANIC LETTERS, 2013, 15 (03) : 566 - 569

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