A NEW VERSION OF THE PETERSON OLEFINATION USING BIS(TRIMETHYLSILYL)METHYL DERIVATIVES AND FLUORIDE-ION AS CATALYST

Reaction between a variety of bis(trimethylsilyl)methyl derivatives and carbonyl compounds under fluoride ion as catalyst is described. The reaction works especially well with nonenolizable carbonyl compounds to give the expected alkenes in high yields and, in some cases, with high stereoselectivity. Application of this methodology to an intramolecular alkenation providing a tricyclic benzocarbacephem ring system is also described. © 1990, American Chemical Society. All rights reserved.