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Synlett 2000; 2000(11): 1549-1552
DOI: 10.1055/s-2000-7940
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Lewis Acid Catalyzed Procedure for Selective Conversion of the Carbocyclic Diels-Alder Adducts of Danishefsky's Diene to 2-Cyclohexenones and Its Extension to Their One-Pot Syntheses

Tsutomu Inokuchi* , Masamitsu Okano, Tomoko Miyamoto, Hariyani Bte Madon, Masaki Takagi
  • *Department of Bioscience and Biotechnology, Faculty of Engineering, Okayama University, Okayama 700-8530, Japan; Fax +81-86-2 51-80 21; E-mail: inokuchi@biotech.okayama-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Conversion of the carbocyclic Diels-Alder adducts of 4-methoxy-2-trimethylsiloxy-1,3-butadiene (Danishefsky's diene), prepared by heating, to the corresponding 2-cyclohexenones was performed cleanly by use of Lewis acids such as Yb(OTf)3 and Bu2BOTf as a catalyst and the selectivity was improved greatly in the bicyclic and tricyclic systems by addition of a small amount of MeOTMS. A one-pot procedure for enone synthesis was also developed for the reactive dienophiles.

Diels-Alder reactions - enones - lanthanides - Lewis acids - eliminations

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