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

Wenting Wu, Zhihui Zhang and Lanny S. Liebeskind*

*Sanford S. Atwood Chemistry Center, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States, Email:

W. Wu, Z. Zhang, L. S. Liebeskind, J. Am. Chem. Soc., 2011, 133, 14256-14259.

DOI: 10.1021/ja2065158


A straightforward trimethylsilylation protocol activates a thiol acid for peptide bond formation at neutral pH using bistrimethylsilylacetamide (BSA). A unique reactivity of the generated O-silylthionoesters toward amines provides oxoamides.

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ID: J48-Y2011-2560