Palladium-Catalyzed Rearrangement of Alkyl Allyl Sulfites to Alkyl Allylsulfonates

Article abstract of DOI:10.1021/jo00293a028

Acyclic and cyclic allyl sulfites undergo a <2,3> rearrangement to furnish allylsulfonates and 1-vinyl-substituted sultones, respectively, by the catalysis of (dba)3Pd2C6H6-triethyl phosphite.Unsymmetrically substituted allylic groups of acyclic allyl sulfites rearrange to provide allylsulfonates with more substituents on the allylic positions.The rearrangement of cis and trans mixtures of cyclic allyl sulfites accompanies the stereochemical isomerization of the substituents and selectively provides trans-1,2-disubstituted sultones.