Highly Enantioselective Copper(I)−Fesulphos-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides
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- 3 November 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (47) , 16394-16395
- https://doi.org/10.1021/ja0552186
Abstract
The catalyst system formed by Cu(CH3CN)4ClO4 and the planar chiral P,S-ligand Fesulphos behaves as a very efficient chiral Lewis acid in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. This catalyst shows a remarkable reactivity at low catalyst loading (0.5−3 mol %), affording in good yields the endo adducts with exceptional levels of enantioselectivity (up to >99% ee). This catalytic asymmetric procedure has a broad structural scope with regard to both azomethine and dipolarophile substitution. The first examples of catalytic asymmetric 1,3-dipolar cycloaddition with ketimine-derived azomethines are reported.Keywords
This publication has 16 references indexed in Scilit:
- Catalytic Enantioselective 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides and Alkenes: The Direct Strategy To Prepare Enantioenriched Highly Substituted Proline DerivativesAngewandte Chemie International Edition in English, 2005
- Lewis Acid Catalyzed Asymmetric Cycloadditions of Nitrones: α′‐Hydroxy Enones as Efficient Reaction PartnersAngewandte Chemie International Edition in English, 2005
- Readily Available Biaryl P,N Ligands for Asymmetric CatalysisAngewandte Chemie International Edition in English, 2004
- Cationic Planar Chiral Palladium P,S Complexes as Highly Efficient Catalysts in the Enantioselective Ring Opening of Oxa‐ and Azabicyclic AlkenesAngewandte Chemie International Edition in English, 2004
- Chiral Copper Complexes of Phosphino Sulfenyl Ferrocenes as Efficient Catalysts for Enantioselective Formal Aza Diels−Alder Reactions of N-Sulfonyl IminesJournal of the American Chemical Society, 2003
- Catalytic Asymmetric [3+2] Cycloaddition of Azomethine Ylides. Development of a Versatile Stepwise, Three-Component Reaction for Diversity-Oriented SynthesisJournal of the American Chemical Society, 2003
- 1-Phosphino-2-sulfenylferrocenes as Planar Chiral Ligands in Enantioselective Palladium-Catalyzed Allylic SubstitutionsThe Journal of Organic Chemistry, 2003
- 1-Phosphino-2-sulfenylferrocenes: efficient ligands in enantioselective palladium-catalyzed allylic substitutions and ring opening of 7-oxabenzonorbornadienesChemical Communications, 2002
- Origins of the Loss of Concertedness in Pericyclic Reactions: Theoretical Prediction and Direct Observation of Stepwise Mechanisms in [3 + 2] Thermal CycloadditionsJournal of the American Chemical Society, 2000
- Stereocontrolled Synthesis of Highly Substituted Proline Esters via [3 + 2] Cycloaddition between N-Metalated Azomethine Ylides and Nitroalkenes. Origins of the Metal Effect on the Stereochemical OutcomeThe Journal of Organic Chemistry, 1998