Ytterbium triflate catalyzed synthesis of alkoxy-substituted donor-acceptor cyclobutanes and their formal [4 + 2] cycloaddition with imines: stereoselective synthesis of piperidines.

Authors

Mahmoud M Abd Rabo Moustafa
Brian L Pagenkopf

Document Type

Article

Publication Date

10-6-2010

Journal

Organic letters

Volume

12

Issue

21

First Page

4732

Last Page

4735

URL with Digital Object Identifier

10.1021/ol102062t

Abstract

A new synthesis of 2-alkoxy-1,1-cyclobutane diesters and their first use in dipolar cycloadditions is reported. Both the formation of the donor-acceptor cyclobutanes and their subsequent annulation with in situ formed imines are catalyzed by Yb(OTf)(3). Cyclobutanes with carbon donor groups give piperidines with high trans stereoselectivity.