Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: Steric control in the [2+2] cycloaddition of singlet oxygen through conformational alignment

被引：65

作者：

Adam, W

Bosio, SG

Turro, NJ

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 30期

关键词：

D O I：

10.1021/ja026815k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The photooxygenation of oxazolidinone-substituted enecarbamates leads to diastereomerically pure dioxetanes. The high diastereoselectivity is rationalized in terms of effective π-facial control achieved by shielding one side of the double bond with the chiral auxiliary. The absolute configuration of the dioxetanes is assigned by derivatization to diols. Copyright © 2002 American Chemical Society.

引用

页码：8814 / 8815

页数：2

共 11 条

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