Organic synthesis using diphenylphosphinoyl as a migrating functional group: diene synthesis

Abstract

Allyldiphenylphosphine oxides can be made from a carbonyl compound, an alkyl halide, and a diphenylphosphinoyl reagent by two routes, one involving migration of the diphenylphosphinoyl group. Lithium derivatives of these allylphosphinic oxides add stereoselectively to aldehydes and the products undergo elimination of diphenylphosphinic acid stereospecifically to give single geometrical isomers of substituted dienes.