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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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

[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.[1]


  1. Silylative Dieckmann-like cyclizations of ester-imides (and diesters). Hoye, T.R., Dvornikovs, V., Sizova, E. Org. Lett. (2006) [Pubmed]
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