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UBC Theses and Dissertations

Silver (I) catalyzed cycloisomerizations of enesulfonamides and enecarbamates Guieb, Krystle Dawn

Abstract

Eight substrates with the general structure 11.0 were synthesized. The substrates differed with respect to the heteroatom tether (X = oxygen or nitrogen), nitrogen protecting group (PG = p-toluenesulfonamide, tert-butylcarbamate, methyl carbamate), and substitution on the ring (Y = H or Ph). Silver (I)-catalyzed cycloisomerizations of the enesulfonamide and enecarbamate substrates successfully gave eight diene products ll.la-h in poor to good yields (36-81%). Diene ll.Ia was also further subjected to the Diels Alder reaction, with acrolein and methacrolein to give tricyclic cycloadducts 11.21a and 11.22a.

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