Amide Formation in One Pot from Carboxylic Acids and Amines via Carboxyl and Sulfinyl Mixed Anhydrides

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.


Published in:
Organic Letters, 15, 10, 2550-2553
Year:
2013
Publisher:
Washington, Amer Chemical Soc
ISSN:
1523-7060
Laboratories:




 Record created 2013-10-01, last modified 2018-12-03


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