Palladium-catalyzed asymmetric ring expansion of allenylcyclobutanols: An asymmetric Wagner-Meerwein shift

被引：95

作者：

Trost, Barry M. ^{[1
]}

Xie, Jia ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 18期

关键词：

D O I：

10.1021/ja0602501

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this study, we developed a palladium-catalyzed atom economic asymmetric Wagner-Meerwein shift of allenylcyclobutanol substrates. It is an excellent method for creating functionalized cyclopentanones with an α-chiral O-tertiary center by ring expansion of allenylcyclobutanols. This reaction was initiated by hydropalladation and afforded excellent enantioselectivity as well as atom economy. This method provides an efficient route toward the synthesis of natural products such as trans-kumausyne's family, spiro ring systems. In addition, we obtained excellent diastereoselectivity and enantioselectivity at the same time by using 3-monosubstituted allenylcyclobutanol. Copyright © 2006 American Chemical Society.

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页码：6044 / 6045

页数：2

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