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Halogenated Oxabicyclo[3.2.1]octadiene Building Blocks: Elaboration of the Dibromoenone

✍ Scribed by Phillip M. Pelphrey; Ravi S. Orugunty; Richard J. Helmich; Merle A. Battiste; Dennis L. Wright

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
194 KB
Volume
2005
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

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 α,β‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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