Enantioselective Nickel-Catalyzed anti-Carbometallative Cyclizations of Alkynyl Electrophiles Enabled by Reversible Alkenylnickel E/Z Isomerization

被引：174

作者：

Clarke, Christopher ^{[1
]}

Incerti-Pradillos, Celia A. ^{[1
]}

Lam, Hon Wai ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

ASYMMETRIC ARYLATIVE CYCLIZATION; REDUCTIVE CYCLIZATION; ARYLBORONIC ACIDS; ORGANOMAGNESIUM COMPOUNDS; ALLYLIC SUBSTITUTION; TRANS-ADDITION; BORONIC ACIDS; RHODIUM; ALCOHOLS; REAGENTS;

D O I：

10.1021/jacs.6b04206

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel-catalyzed additions of arylboronic acids to alkynes, followed by enantioselective cyclizations of the alkenylnickel species onto tethered ketones or enones, are reported. These reactions are reliant upon the formal anti-carbonickelation of the alkyne, which is postulated to occur by the reversible E/Z isomerization of an alkenylnickel species.

引用

页码：8068 / 8071

页数：4

共 46 条

[1] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].

ALLEN, JV ;

COOTE, SJ ;

DAWSON, GJ ;

FROST, CG ;

MARTIN, CJ ;

WILLIAMS, JMJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072

[2] Stereoselective Synthesis of Trisubstituted Alkenes through Sequential Iron-Catalyzed Reductive anti-Carbozincation of Terminal Alkynes and Base-Metal-Catalyzed Negishi CrossCoupling [J].

Cheung, Chi Wai ;

Hu, Xile .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (50) :18439-18444

[3] Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes [J].

Cheung, Chi Wai ;

Zhurkin, Fedor E. ;

Hu, Xile .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (15) :4932-4935

[4] Nickel-Catalyzed Cyclizative trans-Carboboration of Alkynes through Activation of Boron-Chlorine Bonds by Using Organometallic Reagents as Donors of Organic Groups [J].

Daini, Masaki ;

Yamamoto, Akihiko ;

Suginome, Michinori .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (11) :968-976

[5]

Ding A., 2014, COMPREHENSIVE ORGANI, P891

[6] A Broadly Applicable Method for Pd-Catalyzed Carboperfluoro-alkylation of Terminal and Internal Alkynes: A Convenient Route to Tri- and Tetrasubstituted Olefins [J].

Domanski, Sylwester ;

Chaladaj, Wojciech .

ACS CATALYSIS, 2016, 6 (06) :3452-3456

[7] GAMMA-FUNCTIONAL VINYLIC GRIGNARD-REAGENTS .1. REACTIVITY OF ORGANOMAGNESIUM COMPOUNDS WITH ALPHA-ACETYLIC ALCOHOLS IN THE PRESENCE OF CUPROUS HALIDES [J].

DUBOUDIN, JG ;

JOUSSEAUME, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 168 (01) :1-11

[8] Metal mediated carbometallation of alkynes and alkenes containing adjacent heteroatoms [J].

Fallis, AG ;

Forgione, P .

TETRAHEDRON, 2001, 57 (28) :5899-5913

[9] Intramolecular carbolithiation of alkynes:: anti selectivity [J].

Fressigne, Catherine ;

Girard, Anne-Lise ;

Durandetti, Muriel ;

Maddaluno, Jacques .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (05) :891-893

[10] Highly Enantioselective Nickel-Catalyzed Intramolecular Reductive Cyclization of Alkynones [J].

Fu, Wenzhen ;

Nie, Ming ;

Wang, Aizhen ;

Cao, Ziping ;

Tang, Wenjun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (08) :2520-2524

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