Synthesis of Tetrahydro-1,2-oxazines and Pyrrolidines via Cycloadditions of Donor-Acceptor Cyclobutanes and Nitrosoarenes

Authors

Naresh Vemula
Brian L Pagenkopf

Document Type

Article

Publication Date

6-22-2015

Journal

European Journal of Organic Chemistry

Issue

22

First Page

4900

Last Page

4906

URL with Digital Object Identifier

10.1002/ejoc.201500542

Abstract

During efforts to expand the scope of Lewis-acid-catalyzed [4+2] cycloaddition between donor–acceptor cyclobutanes and nitrosoarenes, an unexpected formation of pyrrolidine products was discovered when 50 mol-% of MgI2 was used as a Lewis acid. It was also observed that the electronics of the nitrosoarene and judicious selection of the Lewis acid catalyst have a profound effect on the regioselectivity of the reaction.