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Bicyclo[3.2.1]octane Synthons from Cyclopropenes: Functionalization of Cycloadducts by Nucleophilic Additions

2003; American Chemical Society; Volume: 69; Issue: 2 Linguagem: Inglês

10.1021/jo035240m

1520-6904

Ravi S. Orugunty, Dennis L. Wright, Merle A. Battiste, Richard J. Helmich, Khalil A. Abboud,

Catalytic Alkyne Reactions

It has been known for several decades that a highly functionalized family of tetrahalobicyclo[3.2.1]octadienes are readily available through the cycloaddition of furan or cyclopentadiene with either tetrachloro- or tetrabromocyclopropene. However, the application of these highly functionalized building blocks in synthesis has remained relatively unexplored in relation to their better-known counterparts derived through oxyallyl cation additions. As a first step toward utilizing these highly versatile intermediates in synthesis, a study of the addition of various nucleophiles to the halogenated nucleus has been conducted. It has been found that these halogenated systems are amenable to a wide range of functionalizations in high yields and with good selectivities.