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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: snowdenbama.ua.edu

M. K. Gupta, Z. Li, T. S. Snowden, Org. Lett., 2014, 16, 1602-1605.

DOI: 10.1021/ol500200n (free Supporting Information)


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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.

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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