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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: hoyechem.umn.edu

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

DOI: 10.1021/ol061988q (free Supporting Information)


Abstract

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.

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Key Words

Dieckmann Condensation, N-Heterocycles


ID: J54-Y2006-3550