Enoldiazosulfones for Highly Enantioselective [3+3]-Cycloaddition with Nitrones Catalyzed by Copper(I) with Chiral BOX Ligands

被引：25

作者：

Adly, Frady G. ^{[1
,2
]}

Marichev, Kostiantyn O. ^{[1
]}

Jensen, Joseph A. ^{[1
]}

Arman, Hadi ^{[1
]}

Doyle, Michael P. ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

[2] Univ Canberra, Fac Sci & Technol, Canberra, ACT 2601, Australia

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 01期

基金：

美国国家科学基金会;

关键词：

H INSERTION REACTIONS; BIS(OXAZOLINE) LIGANDS; CYCLOADDITION REACTIONS; CHEMISTRY; DIAZOSULFONES; HETEROCYCLE; SULFONES; ENOLDIAZOACETAMIDES; CYCLOPROPANATION; COMPLEXES;

D O I：

10.1021/acs.orglett.8b03421

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enoldiazosulfones undergo [3 + 3]-cyclo-addition with nitrones when catalyzed by copper (I) catalysts, but not with dirhodium (II) catalysts. Under mild reaction conditions with chiral bisoxazoline ligands, copper (I) catalysts produce 1,2-oxazine-sulfone derivatives in high yields and enantioselectivities. Dirhodium (II) catalysts form stable donor acceptor cyclopropenes that undergo uncatalyzed [3 + 2]-cycloaddition reactions with nitrones.

引用

页码：40 / 44

页数：5

共 44 条

[1]

Ahmad I., 2015, Int. J. Pharm. Pharm. Sci, V7, P19

[2] Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones [J].

Back, Thomas G. ;

Clary, Kristen N. ;

Gao, Detian .

CHEMICAL REVIEWS, 2010, 110 (08) :4498-4553

[3] The Selection of Catalysts for Metal Carbene Transformations [J].

Cheng, Q. -Q. ;

Doyle, M. P. .

ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 66, 2016, 66 :1-31

[4] Vinyldiazo Reagents and Metal Catalysts: A Versatile Toolkit for Heterocycle and Carbocycle Construction [J].

Cheng, Qing-Qing ;

Yu, Yang ;

Yedoyan, Julietta ;

Doyle, Michael P. .

CHEMCATCHEM, 2018, 10 (03) :488-496

[5] Cycloaddition reactions of enoldiazo compounds [J].

Cheng, Qing-Qing ;

Deng, Yongming ;

Lankelma, Marianne ;

Doyle, Michael P. .

CHEMICAL SOCIETY REVIEWS, 2017, 46 (17) :5425-5443

[6] Dirhodium(II)-Catalyzed Annulation of Enoldiazoacetamides with α-Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems [J].

Cheng, Qing-Qing ;

Yedoyan, Julietta ;

Arman, Hadi ;

Doyle, Michael P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) :5573-5576

[7] Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones [J].

Cheng, Qing-Qing ;

Yedoyan, Julietta ;

Arman, Hadi ;

Doyle, Michael P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :44-47

[8] Stereoselective radical C-H alkylation with acceptor/acceptor-substituted diazo reagents via Co(II)-based metalloradical catalysis [J].

Cui, Xin ;

Xu, Xue ;

Jin, Li-Mei ;

Wojtas, Lukasz ;

Zhang, X. Peter .

CHEMICAL SCIENCE, 2015, 6 (02) :1219-1224

[9] SYNTHESIS AND CHEMISTRY OF DONOR-ACCEPTOR-SUBSTITUTED CYCLOPROPENES [J].

DAVIES, HML ;

HOUSER, JH ;

THORNLEY, C .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (23) :7529-7534

[10] Catalytic Divergent [3+3]- and [3+2]-Cycloaddition by Discrimination Between Diazo Compounds [J].

Deng, Yongming ;

Massey, Lynee A. ;

Nunez, Yeray A. Rodriguez ;

Arman, Hadi ;

Doyle, Michael P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (40) :12292-12296

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