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Synlett 1999; 1999(9): 1363-1366
DOI: 10.1055/s-1999-32132
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Formation of Hydrindans and Tricyclo[4.3.0.03,8]nonanes via 6-Endo Trapping of the Nazarov Oxyallyl Intermediate

C. C. Browder* , F. G. West
  • *Department of Chemistry, University of Utah, 315 S. 1400 East, Rm. Dock, Salt Lake City, UT, 84112-0850
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Publication Date:
31 December 1999 (online)

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Treatment of trienones 1a-g with BF3 · OEt2 at - 78 °C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3 + 2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3 · OEt2 led in most cases to a mixture of enones 3 and chloride-trapping products 7.

cyclizations - domino reactions - polycycles - ring closure - tandem reactions

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