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

页码：7721 / 7729

页数：9

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