Stereodivergent Olefination of Enantioenriched Boronic Esters

被引：62

作者：

Armstrong, Roly J. ^{[1
]}

Garcia-Ruiz, Cristina ^{[1
]}

Myers, Eddie L. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 03期

基金：

英国工程与自然科学研究理事会;

关键词：

alkenes; boron; isomers; oxidation; selenium; CROSS-COUPLING REACTIONS; STEREOSPECIFIC CONVERSION; STEREOSELECTIVE-SYNTHESIS; HYDROBORATION-IODINATION; TRISUBSTITUTED OLEFINS; CYCLO-ELIMINATION; ALKENES; ORGANOBORANES; CONVENIENT; MECHANISMS;

D O I：

10.1002/anie.201610387

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition-metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.

引用

页码：786 / 790

页数：5

共 56 条

[1]

[Anonymous], 2001, ANGEW

[2]

Blair D. J., 2014, ANGEW CHEM, V126, P5658

[3] Stereocontrolled Synthesis of Adjacent Acyclic Quaternary-Tertiary Motifs: Application to a Concise Total Synthesis of (-)-Filiformin [J].

Blair, Daniel J. ;

Fletcher, Catherine J. ;

Wheelhouse, Katherine M. P. ;

Aggarwal, Varinder K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5552-5555

[4]

Bonet A, 2014, NAT CHEM, V6, P584, DOI [10.1038/nchem.1971, 10.1038/NCHEM.1971]

[5] VINYLIC ORGANOBORANES .11. A HIGHLY STEREOSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF TRISUBSTITUTED ALKENES VIA ORGANOBORANES [J].

BROWN, HC ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6009-6013

[6] STEREOSPECIFIC CONVERSION OF ALKENYLBORONIC ACIDS INTO ALKENYL BROMIDES WITH INVERSION OF CONFIGURATION - STRIKING DIFFERENCES IN STEREOCHEMISTRY OF REPLACEMENT OF BORONIC ACID SUBSTITUENT BY BROMINE AND IODINE AND ITS SIGNIFICANCE IN TERMS OF REACTION-MECHANISM [J].

BROWN, HC ;

HAMAOKA, T ;

RAVINDRA.N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (19) :6456-6457

[7] REMARKABLE INVERSION IN THE SELECTIVE OXIDATION OF ORGANOBORANES AND THIOETHERS [J].

BROWN, HC ;

MANDAL, AK .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (05) :916-917

[8]

Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO

[9]

2-N

[10] Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].

Cherney, Alan H. ;

Kadunce, Nathaniel T. ;

Reisman, Sarah E. .

CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652

← 1 2 3 4 5 6 →