Functionalization of Double Bonds via Cationic Sulfenyl-X Additions

The addition of cationic sulfenyl halides or other derivatives to double bonds is a well-known reaction [1]. The chemistry of b-heteroatom substituted organic sulfides, the products of these reactions has also been studied [2]. However, relatively little attention has been given to utilizing the addition process as a synthetic method. The work reported here was targeted at studying two potential synthetic applications of cationic arylsulfenyl species addition reactions; first, the preparation of chiral epoxides and, second, the enantioselective cationic cyclization, of polyene substrates. . Sulfenyl cations have previously been used by Livinghouse for cyclization processes but not in chiral fashion.