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Synlett 1996; 1996(7): 669-671
DOI: 10.1055/s-1996-5567
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ortho-Quinone Methide Imine: Generation and Diels-Alder Reaction at Room Temperature

Alain S. Caillé, Laird Trimble, Carl Berthelette, Cheuk K. Lau*
  • *Medicinal Chemistry Department, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, Québec, H9R4P8, Canada, Fax 1 514 6950693; Internet lau@merck.com
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Publication Date:
31 December 2000 (online)

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Inter- and intramolecular Diels-Alder reaction of olefins with ortho-quinone methide imines generated in situ by BF3•Et2O provides an efficient synthesis of tetrahydroquinolines and other polycyclic nitrogen containing heterocycles.

Diels-Alder - quinone methide imine - aza-cannabinoid