Full Chirality Transfer in the Conversion of Secondary Alcohols into Tertiary Boronic Esters and Alcohols Using Lithiation-Borylation Reactions

被引：103

作者：

Bagutski, Viktor ^{[1
]}

French, Rosalind M. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 30期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric synthesis; boronic esters; chirality; quaternary stereocenters; tertiary alcohols; CATALYTIC ENANTIOSELECTIVE CONSTRUCTION; CARBON QUATERNARY STEREOCENTERS; ELECTROPHILIC SUBSTITUTION; ASYMMETRIC-SYNTHESIS; KETONES; GENERATION; REAGENTS; COMPLEXES; EFFICIENT; KETIMINES;

D O I：

10.1002/anie.201001371

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New conditions, full transfer: Using MgBr2/MeOH as an additive now provides essentially 100 % retention of configuration in the lithiation-borylation reaction, thus leading to tertiary boronic esters (or tertiary alcohols) with exceptionally high ee values in all cases - even with rather hindered substrates and more stabilized lithiated carbamates (see scheme; Cb=carbamate, Pin=OCMe2CMe2O). (Figure Presented). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.

引用

页码：5142 / 5145

页数：4

共 28 条

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