82135-89-5Relevant articles and documents
Stereoselective synthesis of medium-sized cyclic compounds by means of tandem reactions of a cyclic oxosulfonium ylide with acetates of Baylis-Hillman adducts
Akiyama, Hitoshi,Fujimoto, Tetsuya,Ohshima, Katsuyoshi,Hoshino, Kenji,Saito, Yuko,Okamoto, Ayu,Yamamoto, Iwao,Kakehi, Akikazu,Iriye, Ryozo
, p. 2265 - 2272 (2007/10/03)
Treatment of a five-membered cyclic oxosulfonium ylide 3 with β-acetoxy-α-methylene ketones in the presence of two equimolar amounts of base afforded the cycloheptene oxide derivatives 7a-i as single stereoisomers in 19-77% yields. The products were considered to form through a Michael-type addition of the ylide, followed by elimination of the acetoxy group and an intramolecular Corey-Chaykovsky reaction. On the other hand, the same treatment, when using a six-membered oxosulfonium ylide, gave the corresponding cyclooctene oxide derivatives in moderate yields, with the products formed in a ca. 4:1 mixture of stereoisomers, a fact correlated with differences in the configuration of the sulfur atom in the sulfinyl group.