Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

被引：229

作者：

Collins, Beatrice S. L. ^{[1
]}

Wilson, Claire M. ^{[1
]}

Myers, Eddie L. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 39期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

asymmetric synthesis; boronic esters; synthetic methods; CATALYZED ENANTIOSELECTIVE DIBORATION; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; SUBSTRATE-CONTROLLED DIASTEREOSELECTIVITIES; ALLYLIC ALCOHOL DERIVATIVES; COPPER(I) BORYL COMPLEXES; N-HETEROCYCLIC CARBENES; ASSEMBLY-LINE SYNTHESIS; CONJUGATE ADDITIONS; STEREOSELECTIVE-SYNTHESIS; ORGANOBORON COMPOUNDS;

D O I：

10.1002/anie.201701963

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Non-racemic chiral boronic esters are recognised as immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups-from amines and halides to arenes and alkynes-along with their air and moisture stability, has established them as an important target for asymmetric synthesis. Efforts towards the stereoselective synthesis of secondary and tertiary alkyl boronic esters have spanned over five decades and are underpinned by a wealth of reactivity platforms, drawing on the unique and varied reactivity of boron. This Review summarizes strategies for the asymmetric synthesis of alkyl boronic esters, from the seminal hydroboration methods of H. C. Brown to the current state of the art.

引用

页码：11700 / 11733

页数：34

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