Silylative Dieckmann-like cyclizations of ester-lmides (and diesters)

Thomas R. Hoye, Vadims Dvornikovs, Elena Sizova

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

Trialkylsilyl triflates effect cyclization of ester-imides such as 2 to produce adducts such as 4a. Trapping of the in situ generated, nucleophilic ketene acetal (cf. 5a) is a key aspect of the transformation. A range of substrates amenable to this operationally simple reaction is reported. In many instances the levels of diastereoselectivity are very high. Mechanistic points are inferred from spectroscopic observations.

Original languageEnglish (US)
Pages (from-to)5191-5194
Number of pages4
JournalOrganic Letters
Volume8
Issue number23
DOIs
StatePublished - Nov 9 2006

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