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Organic letters

Silylative Dieckmann-like cyclizations of ester-imides (and diesters).


PMID 17078675

Abstract

[Structure: see text] 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.

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225649
Trimethylsilyl trifluoromethanesulfonate, 99%
C4H9F3O3SSi