Cascade Reaction of Donor-Acceptor Cyclopropanes: Mechanistic Studies on Cycloadditions with Nitrosoarenes and cis-Diazenes.

Authors

Tristan Chidley
Naresh Vemula
Cheryl A Carson
Michael A Kerr
Brian L Pagenkopf

Document Type

Article

Publication Date

6-2016

Journal

Organic letters

Volume

18

Issue

12

First Page

2922

Last Page

2925

URL with Digital Object Identifier

10.1021/acs.orglett.6b01269

Abstract

Tandem ring opening, elimination, and cycloaddition of donor-acceptor cyclopropanes were observed in Yb(OTf)3-catalyzed cycloaddition with nitrosoarenes. The reaction results in formation of tetrahydro-1,2-oxazine instead of the normal cycloadduct isoxazolidine via in situ nitrone formation. A similar cascade sequence was observed with cis-diazines. Mechanistic studies on this unique transformation offer an entirely new approach for reaction design with donor-acceptor cyclopropanes.