Asymmetric [4+2]-Cycloaddition of Copper-Allenylidenes with Hexahydro-1,3,5-triazines: Access to Chiral Tetrahydroquinazolines

被引：80

作者：

Ji, Danqing ^{[1
]}

Wang, Cheng ^{[1
]}

Sun, Jiangtao ^{[1
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 12期

基金：

中国国家自然科学基金;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; PROPARGYLIC ESTERS; ENANTIOSELECTIVE PROPARGYLATION; 3+2 CYCLOADDITION; BETA-KETOESTERS; 1,3,5-TRIAZINANES; DEAROMATIZATION; ANNULATION; COMPLEXES; IMINES;

D O I：

10.1021/acs.orglett.8b01584

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed asymmetric formal [4 + 2]-cycloaddition of copper-allenylidenes and hexahydro-1,3,5-triazines has been developed, providing chiral tetrahydroquinazolines in moderate to good yields and with high enantioselectivities for most cases (up to 88% yield and 98% ee).

引用

页码：3710 / 3713

页数：4

共 56 条

[1] Transition-Metal-Catalyzed Functionalization of Propargylic Alcohols and Their Derivatives [J].

Bauer, Eike B. .

SYNTHESIS-STUTTGART, 2012, 44 (08) :1131-1151

[2] Asymmetric Catalytic [4+2] Cycloaddition via Cu-Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety [J].

Chen, Hao ;

Lu, Xuehe ;

Xia, Xuejian ;

Zhu, Qiongqiong ;

Song, Yanhong ;

Chen, Jie ;

Cao, Weiguo ;

Wu, Xiaoyu .

ORGANIC LETTERS, 2018, 20 (07) :1760-1763

[3] Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C-N bond formation [J].

Cheng, Li-Jie ;

Brown, Alexander P. N. ;

Cordier, Christopher J. .

CHEMICAL SCIENCE, 2017, 8 (06) :4299-4305

[4] Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex [J].

Cheng, Li-Jie ;

Cordier, Christopher J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) :13734-13738

[5] Enantioselective copper-catalyzed propargylic amination [J].

Detz, Remko J. ;

Delville, Marielle M. E. ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) :3777-3780

[6] Catalyzed Propargylic Substitution [J].

Detz, Remko J. ;

Hiemstra, Henk ;

van Maarseveen, Jan H. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (36) :6263-6276

[7] Catalytic Asymmetric Propargylation [J].

Ding, Chang-Hua ;

Hou, Xue-Long .

CHEMICAL REVIEWS, 2011, 111 (03) :1914-1937

[8] Asymmetric Copper-Catalyzed Propargylic Substitution Reaction of Propargylic Acetates with Enamines [J].

Fang, Ping ;

Hou, Xue-Long .

ORGANIC LETTERS, 2009, 11 (20) :4612-4615

[9] Synthesis of 2-Unsubstituted Pyrrolidines and Piperidines from Donor-Acceptor Cyclopropanes and Cyclobutanes: 1,3,5-Triazinanes as Surrogates for Formylimines [J].

Garve, Lennart K. B. ;

Kreft, Alexander ;

Jones, Peter G. ;

Werz, Daniel B. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (17) :9235-9242

[10] Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes [J].

Gong, Jun ;

Li, Shi-Wu ;

Qurban, Saira ;

Kang, Qiang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (25) :3584-3593

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