A new entry to oxacycles via base-catalyzed endo mode cyclization of allenyl sulfoxides and sulfones.
[reaction: see text]. Treatment of the allenyl sulfoxides and sulfones possessing a proper delta-hydroxy appendage at the C-1 position with potassium tert-butoxide effected endo mode ring closure at the sp-hybridized carbon center of the allenyl moiety to provide the five- to eight-membered oxacycles in high yields.
Mukai
C
C
Faculty of Pharmaceutical Sciences Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan. cmukai@kenroku.kanazawa-u.ac.jp
Yamashita
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H
Hanaoka
M
M
D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D013450:Sulfones / Q000737:chemistry; D013454:Sulfoxides / Q000737:chemistry
D001685:Biological Factors; D004988:Ethers, Cyclic; D013450:Sulfones; D013454:Sulfoxides