Tetrahedron letters

[1, 2]-Wittig rearrangement of a lithioalkyl benzyl ether with inversion of configuration at the carbanion C atom. diastereoselective reductions of cyclohexyl radicals with …

R Hoffmann, T Ru, R Bru

Index: Hoffmann, Rolf; Rueckert, Tanja; Brueckner, Reinhard Tetrahedron Letters, 1993 , vol. 34, # 2 p. 297 - 300

Full Text: HTML

Citation Number: 21

Abstract

Abstract Treatment of the diastereomeric O, Se-ketals cis-or trans-4 with lithium naphthalenide provided, through stereoselective reduction of the radical intermediate 5, the axially lithiated cyclohexyl ether trans-6. trans-6 gave the equatorially benzylated cyclohexanol cis-5 stereoselectively after [1, 2]-Wittig rearrangement and aqueous work-up.