Methanol sulfinyl compounds

The synthesis of enantiomerically pure 2-sulfinyl-l,3-alkadienes has recently been described [38-40]. Maignan and coworkers [39] have reported that condensation of (/ )-(-)-vinyl-p-tolylsulfoxide (26a) with a carbonyl compound such as acetone gave the allylic sulfinylalcohol (27), which, on treatment with N-bromosuccinimide (NBS) in dimethyl sulfide, was converted to the rearranged primary allylic bromide (28) by SN2 displacement. The action of potassium hydroxide in methanol or isopropanol then yielded optically pure 2-p-tolylsulfinyl-1,3-alkadiene (29) by E2 elimination (Scheme 5.9). 

---