Oxidative kinetic resolution-Claisen rearrangement sequence to enantioenriched arylcycloalkenes

被引：12

作者：

Ebner, David C. ^{[1
]}

Novak, Zoltan ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

SYNLETT | 2006年 / 20期

关键词：

oxidative kinetic resolution; Claisen rearrangement; oxidative cyclization; secondary alcohols; palladium catalysis;

D O I：

10.1055/s-2006-958415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Pd-catalyzed oxidative kinetic resolution of secondary alcohols afforded enantioenriched allylic alcohols with high selectivity. These alcohols were transformed into arylcycloalkenes with enantioenriched tertiary and quaternary stereocenters through a two-step vinylation and Lewis acid promoted Claisen rearrangement. Subsequent Pd-catalyzed oxidative cyclization of a Claisen product afforded a 5,5-fused tetrahydrofuran.

引用

页码：3533 / 3539

页数：7

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