Tetrahedron

Stereoselective cyclisation of the 2-allyloxytetrahydropyran-3-yl radical and related species: The influence of anomeric effects

ALJ Beckwith, DM Page

Index: Beckwith, Athelstan L. J.; Page, Dennis M. Tetrahedron, 1999 , vol. 55, # 11 p. 3245 - 3254

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Citation Number: 11

Abstract

Ring closures of the 2-allyloxytetrahydropyran-3-yl radical 1b, its mono-oxa analog 1d and the all carbon system 1a give mainly the cis-fused syn-substituted bicyclononylcarbinyl radicals 2b, 2d and 2a, but the mono-oxa radical 1c gives mainly the cis-fused anti- substituted radical 3c. Molecular mechanics calculations show that the unexpected failure of the dioxa radical 1b to reflect the influence of the anomeric effect on the stereochemistry of ...