Enantioselective synthesis of functionalized fluorinated dihydropyrano [2,3-c]pyrazoles catalyzed by a simple bifunctional diaminocyclohexane-thiourea

被引：31

作者：

Zhang, Hong-Fei ^{[1
]}

Ye, Zheng-Qing ^{[1
]}

Zhao, Gang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 04期

基金：

中国国家自然科学基金;

关键词：

Trifluoromethyl; Pyrazoles; Cyclization; Organocatalysis; ONE-POT SYNTHESIS; ASYMMETRIC MICHAEL ADDITION; NAD(+)-DEPENDENT DNA-LIGASE; CARBONYL-COMPOUNDS; DERIVATIVES; HALOGENATION; ACTIVATION; STRATEGIES; MICROWAVE; ANALOGS;

D O I：

10.1016/j.cclet.2014.01.034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective synthesis of functionalized fluorinated dihydropyrano[2,3-c]pyrazoles has been achieved via a diaminocyclohexane-thiourea catalyzed cascade Michael addition and Thorpe-Ziegler type cyclization in high yields (up to 98%) with moderate to good enantioselectivity (up to 90% ee). (C) 2014 Gang Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：535 / 540

页数：6

共 57 条

[31] Synthesis of Substituted Pyranopyrazoles under Neat Conditions via a Multicomponent Reaction [J].

Nagarajan, Arasampattu S. ;

Reddy, Boreddy S. R. .

SYNLETT, 2009, (12) :2002-2004

[32] Strategies for catalytic asymmetric electrophilic a halogenation of carbonyl compounds [J].

Oestreich, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2324-2327

[33]

Ojima I., 2009, FLUORINE MED CHEM CH

[34] Enantio- and diastereoselective Michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea [J].

Okino, T ;

Hoashi, Y ;

Furukawa, T ;

Xu, XN ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :119-125

[35] Enantioselective Aza-Henry reaction catalyzed by a bifunctional organocatalyst [J].

Okino, T ;

Nakamura, S ;

Furukawa, T ;

Takemoto, Y .

ORGANIC LETTERS, 2004, 6 (04) :625-627

[36] Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts [J].

Okino, T ;

Hoashi, Y ;

Takemoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12672-12673

[37] Surface cleaning under combined microwave and ultrasound irradiation:: flash synthesis of 4H-pyrano[2,3-c]pyrazoles in aqueous media [J].

Peng, Yanqing ;

Song, Gonghua ;

Dou, Ruiling .

GREEN CHEMISTRY, 2006, 8 (06) :573-575

[38] Enantioselective α-fluorination of carbonyl compounds:: Organocatalysis or metal catalysis? [J].

Pihko, PM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (04) :544-547

[39] Construction of asymmetric fluorinated carbon centers [J].

Prakash, GKS ;

Beier, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) :2172-2174

[40] Fluorine in medicinal chemistry [J].

Purser, Sophie ;

Moore, Peter R. ;

Swallow, Steve ;

Gouverneur, Veronique .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (02) :320-330

← 1 2 3 4 5 6 →