1330059-29-4Relevant articles and documents
In situ carboxyl activation using a silatropic switch: A new approach to amide and peptide constructions
Wu, Wenting,Zhang, Zhihui,Liebeskind, Lanny S.
supporting information; experimental part, p. 14256 - 14259 (2011/11/05)
The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1° and 2° amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.