Organic Chemistry Portal



Silylative Dieckmann-Like Cyclizations of Ester-Imides (and Diesters)

Thomas R. Hoye,* Vadims Dvornikovs and Elena Sizova

*Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, Email:

T. R. Hoye, V. Dvornikovs, E. Sizova, Org. Lett., 2006, 8, 5089-5091.

DOI: 10.1021/ol061988q (free Supporting Information)


Trialkylsilyl triflates effect cyclization of ester-imides and diesters. Trapping of the in situ generated, nucleophilic ketene acetal is a key aspect of the transformation. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

see article for more reactions

Key Words

Dieckmann Condensation, N-Heterocycles

ID: J54-Y2006-3550