N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
- 14 May 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (12) , 2333-2336
- https://doi.org/10.1021/ol8004276
Abstract
NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of α-branched aldehydes, a domino amidation−redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.Keywords
This publication has 54 references indexed in Scilit:
- Organocatalysis by N-Heterocyclic CarbenesChemical Reviews, 2007
- N‐Heterocyclic Carbenes as OrganocatalystsAngewandte Chemie International Edition in English, 2007
- Highly Enantioselective Azadiene Diels−Alder Reactions Catalyzed by Chiral N-Heterocyclic CarbenesJournal of the American Chemical Society, 2006
- Extending Mechanistic Routes in Heterazolium Catalysis–Promising Concepts for Versatile Synthetic MethodsAngewandte Chemie International Edition in English, 2005
- Organocatalyzed Conjugate Umpolung of α,β‐Unsaturated Aldehydes for the Synthesis of γ‐ButyrolactonesAngewandte Chemie International Edition in English, 2004
- Catalytic Generation of Activated Carboxylates: Direct, Stereoselective Synthesis of β-Hydroxyesters from EpoxyaldehydesJournal of the American Chemical Society, 2004
- Nucleophilic Carbenes in Asymmetric OrganocatalysisAccounts of Chemical Research, 2004
- A Highly Enantioselective Catalytic Intramolecular Stetter ReactionJournal of the American Chemical Society, 2002
- An Efficient Nucleophilic Carbene Catalyst for the Asymmetric Benzoin CondensationAngewandte Chemie International Edition in English, 2002
- On the Mechanism of Thiamine Action. IV.1 Evidence from Studies on Model SystemsJournal of the American Chemical Society, 1958