An organocatalytic oxidative coupling strategy for the direct synthesis of arylated quaternary stereogenic centers

被引：29

作者：

Bogle, Katherine M.

Hirst, David J.

Dixon, Darren J.

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] GlaxoSmithKline, New Frontiers Sci Pk, Harlow CM19 5AW, Essex, England

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 23期

关键词：

D O I：

10.1021/ol702277v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A broadly applicable oxidative coupling strategy of 3-substituted catechols and carbon-centered pro-nucleophiles for the construction of arylated quaternary stereogenic centers has been developed. Pivoting on a base-catalyzed addition of a carbon-centered acid to an in situ generated o-benzoquinone, the method is general and atom-economical and provides remarkably efficient access to one of the most challenging structural motifs. Furthermore, use of chiral bifunctional organocatalysts allows the process to be rendered asymmetric (up to 81% ee).

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收藏

页码：4901 / 4904

页数：4

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