A highly stereoselective and recyclable microgel-supported bifunctional sulfonamide organocatalyst for asymmetric alcoholysis of meso-cyclic anhydrides: a thermo-responsive "organic nanoreactor"

被引：4

作者：

Xiong, Fei ^{[1
]}

Ma, Chao ^{[1
]}

Zhu, Yi-Ren ^{[1
]}

Sun, Chen ^{[1
]}

Chen, Lu ^{[1
]}

Zhang, Yan-Jun ^{[1
]}

Zhu, Yuan-Jie ^{[1
]}

Wang, Zhong-Hua ^{[2
]}

机构：

[1] Univ Shanghai Sci & Technol, Dept Chem, Shanghai 200093, Peoples R China

[2] Shanghai Inst Technol, Sch Chem & Environm & Engn, Shanghai 201400, Peoples R China

来源：

NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 27期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE ALCOHOLYSIS; DESYMMETRIZATION; CATALYSTS; NANOPARTICLES; EFFICIENT;

D O I：

10.1039/d2nj01914k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel thermosensitive bifunctional sulfonamide microgel catalyst was synthesized by immobilization on a highly cross-linked three-dimensional network structure through covalent interactions. The microgel-supported organocatalyst has been successfully applied to catalyze the asymmetric alcoholysis reaction in high yields and good stereoselectivity (up to 90% ee). Furthermore, the polymeric catalysts could be recovered easily and reused multiple times (5 runs) without apparent loss of catalytic activity and enantioselectivity.

引用

页码：13269 / 13274

页数：6

共 45 条

[11] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts [J].

Connon, Stephen J. .

CHEMICAL COMMUNICATIONS, 2008, (22) :2499-2510

[12] Preparation of microgel-supported chiral catalysts and their application in the asymmetric hydrogenation of aromatic ketones [J].

Deng, Jia ;

Lu, Cuifen ;

Yang, Guichun ;

Chen, Zuxing .

REACTIVE & FUNCTIONAL POLYMERS, 2012, 72 (06) :378-382

[13] Recent advances in enantioselective organocatalyzed anhydride desymmetrization and its application to the synthesis of valuable enantiopure compounds [J].

Diaz de Villegas, Maria D. ;

Galvez, Jose A. ;

Etayo, Pablo ;

Badorrey, Ramon ;

Lopez-Ram-de-Viu, Pilar .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (11) :5564-5587

[14] Asymmetric organocatalysis: From infancy to adolescence [J].

Dondoni, Alessandro ;

Massi, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660

[15] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[16] Gold-Nanoparticle-Embedded Poly(N-isopropylacrylamide) Microparticles for Selective Quasi-Homogeneous Catalytic Homocoupling Reactions [J].

Eyimegwu, Pascal N. ;

Lartey, Jemima A. ;

Kim, Jun-Hyun .

ACS APPLIED NANO MATERIALS, 2019, 2 (09) :6057-6066

[17] Engineering of silver nanoparticle fabricated poly (N-isopropylacrylamide-co-acrylic acid) microgels for rapid catalytic reduction of nitrobenzene [J].

Farooqi, Zahoor H. ;

Naseem, Khalida ;

Ijaz, Aysha ;

Begum, Robina .

JOURNAL OF POLYMER ENGINEERING, 2016, 36 (01) :87-96

[18] The immobilisation of chiral organocatalysts on magnetic nanoparticles: the support particle cannot always be considered inert [J].

Gleeson, Oliver ;

Davies, Gemma-Louise ;

Peschiulli, Aldo ;

Tekoriute, Renata ;

Gun'ko, Yurii K. ;

Connon, Stephen J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) :7929-7940

[19] The 2021 chemistry Nobel laureates and asymmetric organocatalysis [J].

Hargittai, Istvan .

STRUCTURAL CHEMISTRY, 2022, 33 (01) :303-305

[20] Bronsted Acid/Lewis Base Hybrid Complexes [J].

Hatano, Manabu ;

Ishihara, Kazuaki .

CHIRAL LEWIS ACIDS, 2018, 62 :91-120

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