Regio- and stereoselective addition of N-p-tosyl-trichloromethylimine to vinyl dihydronaphthalenes |
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| Authors: | RP Loven WA Zunnebeld WN Speckamp |
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| Institution: | Laboratory for Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, Amsterdam, The Netherlands |
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| Abstract: | Imine 1 underwent regioselective addition to vinyl dihydronaphthalenes 2 and 3 to afford the cyclo-adducts 4, 5 and 6. The structures and stereochemistry of the latter adducts have been determined by PMR and X-ray analysis. Factors influencing the mode of addition are discussed. Epoxidation and bromination of 4 led to the formation of aromatizated products. Hydrolysis of 5 and 6 gave the corresponding ketones which underwent facile ringopening via a retro-Michael type of reaction. |
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| Keywords: | To whom all inquiries should be directed |
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