Preparation of One-Carbon Homologated Amides from Aldehydes or Primary Alcohols
Manoj K. Gupta, Zhexi Li and Timothy S. Snowden *
*Department of Chemistry, The University of Alabama, Box
870336, Tuscaloosa, Alabama 35487-0336, United States, Email: snowden
bama.ua.edu
M. K. Gupta, Z. Li, T. S. Snowden, Org. Lett., 2014, 16, 1602-1605.
DOI: 10.1021/ol500200n
see article for more reactions
Abstract
Aldehydes and primary alcohols can be converted via tricholormethyl carbinols to one-carbon homologated primary, secondary, or tertiary amides. The approach tolerates (hetero)aryl, alkyl, alkenyl, and racemizable chiral substrates, offers the opportunity to employ unprotected amino acids as amine sources and enables the preparation of Weinreb amides from aryl and unhindered aliphatic substrates.
see article for more examples
proposed reaction pathway
General and Practical Conversion of Aldehydes to Homologated Carboxylic Acids
L. R. Cafiero, T. S. Snowden, Org. Lett., 2008, 10, 3853-3856.
Key Words
Jocic Reaction, Hydrolysis, Amidation, Sodium Borohydride
ID: J54-Y2014
