Halogenated oxabicyclo[3.2.1]octadiene building blocks: Elaboration of the dibromoenone

被引：12
|
作者：
Pelphrey, PM [1 ]
Orugunty, RS
Helmich, RJ
Battiste, MA
Wright, DL
机构：
[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA
[2] Univ Florida, Dept Chem, Gainesville, FL 32611 USA
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 20期
关键词：
cross-coupling; dibromoenone; oxygen heterocycles; palladium;
D O I：
10.1002/ejoc.200500529
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have been interested in exploiting the highly functionalized oxabicyclo[3.2.1]octadienes that are produced by the cycloaddition of furan and tetrabromocyclopropene as synthetic building blocks. As part of this program, we have prepared non-racemic derivatives of these adducts containing an alpha,beta-dibromoenone moiety embedded in the bicyclic framework. Elaboration of this unit has been realized through substitution and palladium-catalyzed cross-coupling reactions. Formation of bicyclodecenes has also been accomplished by a chromium-nickel-mediated ring closure. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
引用
收藏
页码：4296 / 4303
页数：8
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