دورية
Stereoselective Synthesis of Medium‐Sized Cyclic Compounds by Means of Tandem Reactions of a Cyclic Oxosulfonium Ylide with Acetates of Baylis−Hillman Adducts
| العنوان: | Stereoselective Synthesis of Medium‐Sized Cyclic Compounds by Means of Tandem Reactions of a Cyclic Oxosulfonium Ylide with Acetates of Baylis−Hillman Adducts |
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| المؤلفون: | Akiyama, Hitoshi, Fujimoto, Tetsuya, Ohshima, Katsuyoshi, Hoshino, Kenji, Saito, Yuko, Okamoto, Ayu, Yamamoto, Iwao, Kakehi, Akikazu, Iriye, Ryozo |
| المصدر: | European Journal of Organic Chemistry; June 2001, Vol. 2001 Issue: 12 p2265-2272, 8p |
| مستخلص: | Treatment of a five‐membered cyclic oxosulfonium ylide 3with β‐acetoxy‐α‐methylene ketones in the presence of two equimolar amounts of base afforded the cycloheptene oxide derivatives 7a−ias 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. |
| قاعدة البيانات: | Supplemental Index |
| تدمد: | 1434193X 10990690 |
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| DOI: | 10.1002/1099-0690(200106)2001:12<2265::AID-EJOC2265>3.0.CO;2-8 |