Chiral copper-catalyzed enantioselective Michael difluoromethylation of arylidene meldrum's acids with (difluoromethyl)zinc reagents

被引：14

作者：

Endo, Yu ^{[1
]}

Ishii, Koki ^{[1
]}

Mikami, Koichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Sch Mat & Chem Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON | 2019年 / 75卷 / 31期

基金：

日本科学技术振兴机构;

关键词：

ARYL BORONIC ACIDS; MEDIATED DIFLUOROMETHYLATION; ARYLBORONIC ACIDS; FLUORINE; HALIDES; ARENES; TRIFLUOROMETHYLATION; IODIDES;

D O I：

10.1016/j.tet.2019.05.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic enantioselective difluoromethylation of arylidene Meldrum's acids with (difluoromethyl) zinc reagent, easily prepared through zinc/iodide exchange reaction of difluoroiodomethane and diethylzinc with co-solvent such as pyridines, by a chiral phosphoramidite-Cu catalyst is shown to provide highly enantioselective sp [3]-difluoromethyl Michael addition product in good yields and high levels of enantioselectivity. (C) 2019 Published by Elsevier Ltd.

引用

页码：4099 / 4103

页数：5

共 46 条

[1] Copper-catalyzed allylic difluoromethylation of allyl carbonates with (difluoromethyl)zinc reagent [J].

Aikawa, Kohsuke ;

Ishii, Koki ;

Endo, Yu ;

Mikami, Koichi .

JOURNAL OF FLUORINE CHEMISTRY, 2017, 203 :122-129

[2] Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent [J].

Aikawa, Kohsuke ;

Serizawa, Hiroki ;

Ishii, Koki ;

Mikami, Koichi .

ORGANIC LETTERS, 2016, 18 (15) :3690-3693

[3] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[4] Bulky Diamine Ligand Promotes Cross-Coupling of Difluoroalkyl Bromides by Iron Catalysis [J].

An, Lun ;

Xiao, Yu-Lan ;

Zhang, Shu ;

Zhang, Xingang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (23) :6921-6925

[5] Pd-Catalyzed Transfer of Difluorocarbene [J].

Deng, Xiao-Yun ;

Lin, Jin-Hong ;

Xiao, Ji-Chang .

ORGANIC LETTERS, 2016, 18 (17) :4384-4387

[6] Nucleophilic trifluoromethylation of arylidenemalononitriles [J].

Dilman, Alexander D. ;

Levin, Vitalij V. ;

Belyakov, Pavel A. ;

Struchkova, Marina I. ;

Tartakovsky, Vladimir A. .

TETRAHEDRON LETTERS, 2008, 49 (28) :4352-4354

[7]

Feng Z, 2017, NAT CHEM, V9, P918, DOI [10.1038/NCHEM.2746, 10.1038/nchem.2746]

[8] Access to Difluoromethylated Arenes by Pd-Catalyzed Reaction of Arylboronic Acids with Bromodifluoroacetate [J].

Feng, Zhang ;

Min, Qiao-Qiao ;

Zhang, Xingang .

ORGANIC LETTERS, 2016, 18 (01) :44-47

[9] Palladium-Catalyzed Difluoromethylation of Aryl Chlorides and Bromides with TMSCF2H [J].

Ferguson, Devin M. ;

Malapit, Christian A. ;

Bour, James R. ;

Sanford, Melanie S. .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06) :3735-3740

[10] Copper-Mediated Difluoromethylation of Aryl and Vinyl Iodides [J].

Fier, Patrick S. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5524-5527

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