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
收藏
页码：3498 / 3501
页数：4
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