Catalyst-controlled enantioselective 1,1-arylboration of unactivated olefins

被引：100

作者：

Wang, Wang ^{[1
]}

Ding, Chao ^{[1
]}

Yin, Guoyin ^{[1
]}

机构：

[1] Wuhan Univ, Inst Adv Studies, Wuhan, Peoples R China

来源：

NATURE CATALYSIS | 2020年 / 3卷 / 11期

基金：

中国国家自然科学基金;

关键词：

FUNCTIONALIZATION; ALKENES; DIFUNCTIONALIZATION; ARYLBORATION;

D O I：

10.1038/s41929-020-00523-8

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Enantioselective difunctionalization of alkenes constitutes an efficient strategy to assemble complex chiral molecules from simple racemic or achiral starting materials. Here we present an intermolecular nickel-catalysed enantioselective 1,1-arylboration of unactivated terminal alkenes. The high regio- and enantioselectivities of the reactions arise from a judicious choice of the nickel catalyst rather than the incorporation of a directing group. Moreover, excellent regioselectivities can also be obtained from the reactions of allylbenzenes. We also conducted a series of stereospecific downstream transformations for the enantioenriched secondary boronic esters. These examples represent an efficient catalyst-controlled enantioselective 1,1-difunctionalization of unactivated alkenes.

引用

收藏

页码：951 / 958

页数：8

相关论文

共 48 条

[1] Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes [J].

Anthony, David ;

Lin, Qiao ;

Baudet, Judith ;

Diao, Tianning .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (10) :3198-3202

[2] Nickel-Catalyzed Borylation of Benzylic Ammonium Salts: Stereospecific Synthesis of Enantioenriched Benzylic Boronates [J].

Basch, Corey H. ;

Cobb, Kelsey M. ;

Watson, Mary P. .

ORGANIC LETTERS, 2016, 18 (01) :136-139

[3] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[4] Catalyst-Controlled 1,2-and 1,1-Arylboration of -Alkyl Alkenyl Arenes [J].

Bergmann, Allison M. ;

Dorn, Stanna K. ;

Smith, Kevin B. ;

Logan, Kaitlyn M. ;

Brown, M. Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) :1719-1723

[5] The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles [J].

Chemler, Sherry R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) :3009-3019

[6] Nickel-Catalyzed Arylboration of Alkenylarenes: Synthesis of Boron-Substituted Quaternary Carbons and Regiodivergent Reactions [J].

Chen, Liang-An ;

Lear, Alan R. ;

Gao, Pin ;

Brown, M. Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) :10956-10960

[7] Asymmetric remote C-H borylation of internal alkenes via alkene isomerization [J].

Chen, Xu ;

Cheng, Zhaoyang ;

Guo, Jun ;

Lu, Zhan .

NATURE COMMUNICATIONS, 2018, 9

[8] Asymmetric Synthesis of Secondary and Tertiary Boronic Esters [J].

Collins, Beatrice S. L. ;

Wilson, Claire M. ;

Myers, Eddie L. ;

Aggarwal, Varinder K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) :11700-11733

[9] Catalytic Enantioselective Functionalization of Unactivated Terminal Alkenes [J].

Coombs, John R. ;

Morken, James P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) :2636-2649

[10]

DeRosa T.F., 2006, ADV SYNTHETIC ORGANI

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