Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles
The Journal of Organic Chemistry2007Vol. 72(5), pp. 1811–1813
Citations Over TimeTop 10% of 2007 papers
Abstract
Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyzed decomposition of the diazo compound in the presence of the imine presumably generates a transient azomethine ylide that undergoes cycloaddition with dipolarophiles in a highly convergent manner.
Related Papers
- → Asymmetric approach to the pentacyclic skeleton of Aspidosperma alkaloids via enantioselective intramolecular 1,3-dipolar cycloaddition of carbonyl ylides catalyzed by chiral dirhodium(II) carboxylates(2009)59 cited
- → Catalytic Enantioselective Tandem Carbonyl Ylide Formation/1,3‐Dipolar Cycloaddition Reactions of α‐Diazo Ketones with Aromatic Aldehydes using Dirhodium(II) Tetrakis[N‐benzene‐fused‐phthaloyl‐(S)‐valinate](2007)58 cited
- → Model Studies Directed toward the Total Synthesis of (±)-Ribasine. A Tandem Cyclization−Cycloaddition Route Leading to the Core Skeleton(1999)56 cited
- → Dirhodium(ii) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomünchnones), an approach to analogues of dehydrogliotoxin(2003)23 cited
- → A convenient one-pot approach to Paclitaxel (Taxol) side chain via 1,3-dipolar cycloaddition of carbonyl ylides and N -benzoylbenzyl imines(2018)6 cited