Iridium-Catalyzed Selective α-Alkylation of Unactivated Amides with Primary Alcohols
Authors:
- 15 February 2013
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (5) , 1144-1147
Abstract
The first α-alkylation of unactivated amides with primary alcohols is described. An effective and robust iridium pincer complex has been developed for selective α-alkylation of tertiary and secondary acetamides involving a “borrowing hydrogen” methodology. The method is compatible with alcohols bearing various functional groups. This presents a convenient and environmentally benign protocol for α-alkylation of amides.Keywords
This publication has 35 references indexed in Scilit:
- The Catalytic Amination of AlcoholsChemCatChem, 2011
- Organic Synthesis Involving Iridium-Catalyzed OxidationChemical Reviews, 2011
- Iridium-Catalyzed Reactions Involving Transfer Hydrogenation, Addition, N-Heterocyclization, and Alkylation Using Alcohols and Diols as Key SubstratesSynlett, 2010
- Iridium-Catalyzed Hydrogen Transfer Reactions2010
- The Give and Take of Alcohol ActivationScience, 2010
- Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal CatalysisChemical Reviews, 2009
- Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as ElectrophilesChemical Reviews, 2009
- Asymmetric Total Syntheses of (+)-3-(Z)-Laureatin and (+)-3-(Z)-Isolaureatin by “Lone Pair−Lone Pair Interaction-Controlled” IsomerizationJournal of the American Chemical Society, 2007
- Solid-Phase Unnatural Peptide Synthesis (UPS)Journal of the American Chemical Society, 1996
- Modification of Cyclosporin A (CS): Generation of an enolate at the sarcosine residue and reactions with electrophilesHelvetica Chimica Acta, 1993