Transition-Metal-Free Homologative Cross-Coupling of Aldehydes and Ketones with Geminal Bis(boron) Compounds

被引：56

作者：

Stephens, Thomas C. ^{[1
]}

Pattison, Graham ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Gibbet Hill Rd, Coventry CV4 7AL, W Midlands, England

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 13期

关键词：

HYDROXYL BORONIC ESTERS; ALLYLIC SUBSTITUTION; CARBONYL-COMPOUNDS; ARYLBORONIC ACIDS; ALKYL-HALIDES; DIASTEREOSELECTIVE SYNTHESIS; DEHYDROGENATIVE BORYLATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; GEM-SILYLBORYLATION;

D O I：

10.1021/acs.orglett.7b01474

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks. which provides the coupled, homologated carbonyl compound, upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces anew carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.

引用

页码：3498 / 3501

页数：4

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