Cu-Catalyzed 1,3-migration of phosphate group: Synthesis of phosphatyloxy-containing heterocycles

ORGN 487

Dmitrijs Cernaks, dchern2@uic.edu and Vladimir Gevorgyan, vlad@uic.edu. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street 4500SES, Chicago, IL 60607
In continuation of our studies on the development of novel methods for the synthesis of heterocycles we found that phosphatyloxy-substituted alkynyl ketones 1 and imines 2 undergo facile Cu-catalyzed cycloisomerization reaction with concomitant 1,3-migration of phosphatyloxy group to form furans 3 and indolizines 4 in good yield. It was also found that phosphatyloxy heterocycles 3 and 4 can be efficiently functionalized via Kumada cross-coupling protocol to give alkyl- and aryl-substituted derivatives 5 and 6, respectively.