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
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.
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页码:8814 / 8815
页数:2
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