Syntheses with Sulfones L : Preparation of β-Hydroxysulfones through the Combined Oxidative Desulfonylation/Condensation Reaction of Sulfonyl Anions. Application to Terpene Synthesis.

Article abstract of DOI:10.1016/S0040-4039(01)91350-4

The oxidative desulfonylation of primary sulfonyl anions with the molybdenum peroxide reagent, MoO⁵.Py.HMPA, leads directly to β-hydroxysulfones through condensation of the starting α-sulfonyl anion with the aldehyde formed in situ.Symmetrical polyenes such as (Z)-12-dehydrosqualene and (Z)-16-phytoene have been obtained in three steps in > 87percent stereoslectivity from the corresponding β-hydroxysulfones.