Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Study of cis/trans and endo/exo Diastereoselectivity in the [4+3]-Cycloaddition Reaction of 2-Functionalized Furans and Dimethyloxyallyl Cation: Preparation of Versatile Cycloheptane Synthons
Angel M. MontañaSandra RibesPedro M. GrimaFrancisca García
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1997 Volume 26 Issue 9 Pages 847-848


A study on the influence of steric and electronic effects of a function attached at C-2 of furans in the yield and diastereoselectivity of [4+3] cycloaddition reactions with oxyallyl cations is presented. In almost all studied furans a cis diastereospecificity and a high endo diastereoselectivity is observed. Increasing bulkyness of the function attached at C-2 of furans, increases the endo diastereoselectivity, but decreases yield. Increasing the electronic density of the furan system, by an electron donating group attached at C-2, increases yield and diastereoselectivity.

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© 1997 The Chemical Society of Japan
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