title: Amide formation in one pot from carboxylic acids and amines via carboxyl and sulfinyl mixed anhydrides.
abstract: An efficient method has been developed for the preparation of yet unknown acyclic mixed anhydrides of carboxylic and sulfinic acids. Sterically hindered 2-methylbut-3-ene-2-sulfinyl carboxylates add primary and secondary amines preferentially onto the carbonyl moieties realizing a new method for the one-pot preparation of carboxamides. It uses 1:1 mixtures of carboxylic acids and amines without a base, requires no excess of reagents, and liberates only volatile coproducts. Protected di- and tripeptides have been prepared in solution without epimerization by application of this method.
authors: Laboratory of Glycochemistry and Asymmetric Synthesis, Swiss Federal Institute of Technology (EPFL) , CH 1015 Lausanne, Switzerland.
authors: Bartosz K
authors: BK
authors: Zambroń
authors: Srinivas R
authors: SR
authors: Dubbaka
authors: Dean
authors: D
authors: Marković
authors: Elena
authors: E
authors: Moreno-Clavijo
authors: Pierre
authors: P
authors: Vogel
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D000588:Amines; D000812:Anhydrides; D002264:Carboxylic Acids; D013452:Sulfonium Compounds