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In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

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journal contribution
posted on 14.09.2011, 00:00 by Wenting Wu, Zhihui Zhang, Lanny S. Liebeskind
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.

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