3-Aza-5-alkenols undergo selective 7- endo - trig cyclization when treated with a catalytic Pd(II) species, CuCl2and ArSnBu3giving 7-aryl-substituted oxazepanes. The intramolecular alkoxylation occurs with formation of a seven-membered ring only when associated with an arylating step. Otherwise, 6- exo-trig reactions, providing morpholine derivatives, were observed.
Selective 7- endo -Cyclization of 3-Aza-5-alkenols through Oxidative Pd(II)-Catalyzed Olefin Oxyarylation
Gazzola, Silvia;Borelli, Tea;Diamante, Daria;Broggini, Gianluigi
2018-01-01
Abstract
3-Aza-5-alkenols undergo selective 7- endo - trig cyclization when treated with a catalytic Pd(II) species, CuCl2and ArSnBu3giving 7-aryl-substituted oxazepanes. The intramolecular alkoxylation occurs with formation of a seven-membered ring only when associated with an arylating step. Otherwise, 6- exo-trig reactions, providing morpholine derivatives, were observed.
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