title: In situ carboxyl activation using a silatropic switch: a new approach to amide and peptide constructions.
abstract: 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.
authors.affiliation: Sanford S. Atwood Chemistry Center, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
authors.forename: Wenting
authors.initials: W
authors.lastname: Wu
authors.forename: Zhihui
authors.initials: Z
authors.lastname: Zhang
authors.forename: Lanny S
authors.initials: LS
authors.lastname: Liebeskind
mesh_terms: D000081:Acetamides / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry
chemical_list: D000081:Acetamides; D000577:Amides; D010455:Peptides; D011725:Pyridines; D014297:Trimethylsilyl Compounds; C034960:oxoamide