Protodeboronation of Tertiary Boronic Esters: Asymmetric Synthesis of Tertiary Alkyl Stereogenic Centers

被引：184

作者：

Nave, Stefan ^{[1
]}

Sonawane, Ravindra P. ^{[1
]}

Elford, Tim G. ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; CHIRAL SECONDARY; B-ALKYLCATECHOLBORANES; ORGANOBORONIC ESTERS; CONJUGATE ADDITIONS; ALLYLIC ALKYLATIONS; QUATERNARY CARBONS; CONVERSION; OLEFINS; HYDROGENATION;

D O I：

10.1021/ja1084207

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF center dot 3H(2)O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. The methodology has been applied to a short synthesis of the sesquiterpene, (S)-turmerone.

引用

页码：17096 / 17098

页数：3

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