Substrate-controlled stereoselectivity in the Yamamoto aldol reaction

被引：18
|
作者：
Schlaeger, Nadin
Kirschning, Andreas [1 ]
机构：
[1] Inst Organ Chem, D-30167 Hannover, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 38期
关键词：
EXCEPTIONAL CHELATING ABILITY; CARBONYL ADDITION-REACTIONS; VINYLOGOUS ALDOL; 1,3-DIOL ACETONIDES; ALUMINUM TRIS(2,6-DIPHENYLPHENOXIDE); DIMETHYLALUMINUM CHLORIDE; METHYLALUMINUM DICHLORIDE; TITANIUM TETRACHLORIDE; CHITINOPHAGA-SANCTI; CARBOXYLIC ESTERS;
D O I：
10.1039/c2ob26185e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Yamamoto aldol reaction is a vinylogous aldol reaction that relies on bulky aluminium-based Lewis acids. These activate both the aldehyde as well as become part of the enolate moiety. The report discloses the first detailed study on the substrate-controlled Yamamoto aldol reaction in which 2,3-syn and 2,3-anti disubstituted aldehydes serve as the stereodirecting elements. The "size" of the substituent in the beta-position strongly determines the facial selectivity of enolate addition to the aldehyde. Large substituents favour formation of 1,3-syn diols while slim alkynyl groups preferentially lead to 1,3-anti products.
引用
收藏
页码：7721 / 7729
页数：9
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