Pummerer Reaction of Thienamycin-Type Cyclic Vinylogous Sulfide and Sulfoxide

抄録

The Pummerer reaction of the thienamycin-type cyclic vinylogous sulfide (4) and sulfoxide (5) was studied. When the sulfide (4) was treated with tert-BuOCl and MeOH in the presence of Ag₂O, an additive-type Pummerer reaction took place to produce 17 instead of the normal rearranged product (6). The sulfoxide (5), on treatment with Ac₂O, (CF₃CO)₂O, and 2, 4, 6-collidine, underwent an intramolecular additive-type Pummerer reaction to give the bicyclic compound (19) as a main product. In the reaction of the alkoxysulfonium salt (25) with 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), Pummerer-type rearrangement took place, giving the methoxy compound (6) in poor yield.