NHC-catalyzed [4+2] cycloaddition reactions for the synthesis of 3′-spirocyclic oxindoles via a C-F bond cleavage protocol

被引：27

作者：

Yan, Jun ^{[1
]}

Shi, Kuangxi ^{[1
]}

Zhao, Chengtao ^{[1
]}

Ding, Liyuan ^{[1
]}

Jiang, Shengsheng ^{[1
]}

Yang, Limin ^{[1
]}

Zhong, Guofu ^{[1
]}

机构：

[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 310018, Zhejiang, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 13期

关键词：

N-HETEROCYCLIC CARBENE; DIELS-ALDER REACTIONS; HIGHLY ENANTIOSELECTIVE ROUTE; OXIDATIVE GAMMA-ADDITION; METAL-COMPLEXES; ALPHA; BETA-UNSATURATED ALDEHYDES; CARBAZOLESPIROOXINDOLE SKELETONS; QUATERNARY STEREOCENTERS; SPIROCYCLIC OXINDOLES; COOPERATIVE CATALYSIS;

D O I：

10.1039/c7cc08048d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral NHC-catalyzed cycloaddition of gamma-fluoroenals is developed. The nucleophilic gamma-carbon generated via C-F bond cleavage undergoes highly enantioselective cycloaddition (up to >99% ee) to isatins and provides 3 '-spirocyclic oxindoles in good yields (up to 91%).

引用

页码：1567 / 1570

页数：4

共 112 条

[1] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[2] A new route to diastereomerically pure cyclopropanes utilizing stabilized phosphorus ylides and γ-hydroxy enones derived from 1,2-dioxines:: Mechanistic investigations and scope of reaction [J].

Avery, TD ;

Taylor, DK ;

Tiekink, ERT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5531-5546

[3] Strategies for the enantioselective synthesis of spirooxindoles [J].

Ball-Jones, Nicolas R. ;

Badillo, Joseph J. ;

Franz, Annaliese K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181

[4] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[5] ON THE MECHANISM OF THIAMINE ACTION .4. EVIDENCE FROM STUDIES ON MODEL SYSTEMS [J].

BRESLOW, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (14) :3719-3726

[6] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[7] Manganese-catalyzed synthesis of monofluoroalkenes via C-H activation and C-F cleavage [J].

Cai, Sai-Hu ;

Ye, Lu ;

Wang, Ding-Xing ;

Wang, Yi-Qiu ;

Lai, Lin-Jie ;

Zhu, Chuan ;

Feng, Chao ;

Loh, Teck-Peng .

CHEMICAL COMMUNICATIONS, 2017, 53 (62) :8731-8734

[8] Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].

Cárdenas, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387

[9] Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes [J].

Chan, Audrey ;

Scheidt, Karl A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5334-+

[10] Synthesis of spiropyrazoline oxindoles by a formal [4+1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3-dienes [J].

Chen, Dong-Zhen ;

Xiao, Wen-Jing ;

Chen, Jia-Rong .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07) :1289-1293

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