Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones
- 29 May 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (12), 8142-8148
- https://doi.org/10.1021/acs.joc.0c01023
Abstract
The asymmetric 1,3-dipolar cycloaddition of glycine imino esters to 1-propene-1,3-sultone or sulfocoumarins is described. The reaction was efficiently catalyzed by Cu(MeCN)4BF4/DTBM-Segphos or Cu(MeCN)4BF4/tBu-FcPhox at room temperature to afford fused pyrrolidines as single regioisomers with excellent diastereoselectivity and enantioselectivity. The broad substrate scope of this reaction provides convenient access to structurally diverse multisubstituted pyrrolidines in an optically pure fashion.Keywords
Funding Information
- Kato Memorial Bioscience Foundation
- Japan Society for the Promotion of Science (JP19K23637, JP20K15288)
This publication has 37 references indexed in Scilit:
- Diastereodivergent Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides and β-Fluoroalkyl Vinylsulfones: Low Copper(II) Catalyst Loading and Theoretical StudiesAngewandte Chemie-International Edition, 2019
- Stereochemical diversity in pyrrolidine synthesis by catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylidesChemical Communications, 2019
- Switching Diastereoselectivity in Catalytic Enantioselective (3+2) Cycloadditions of Azomethine Ylides Promoted by Metal Salts and Privileged Segphos-Derived LigandsThe Journal of Organic Chemistry, 2019
- Ligand-controlled switch in diastereoselectivities: catalytic asymmetric construction of spirocyclic pyrrolidine-azetidine/oxe(thie)tane derivativesChemical Communications, 2019
- Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic AlkenesThe Journal of Organic Chemistry, 2017
- Recent advances in the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and dipolarophilesTetrahedron: Asymmetry, 2017
- Current Trends towards the Synthesis of Bioactive Heterocycles and Natural Products Using 1,3-Dipolar Cycloadditions (1,3-DC) with Azomethine YlidesSynthesis, 2017
- Recent Advances of Catalytic Asymmetric 1,3-Dipolar CycloadditionsChemical Reviews, 2015
- Regio- and stereoselective synthesis of isoxazolidine derivatives by asymmetric 1,3-dipolar cycloaddition reaction of chiral nitrones with 1-propene-1,3-sultoneJournal of Heterocyclic Chemistry, 2008
- Synthesis of chiral sultams and their application as chiral auxiliaries in an asymmetric Diels–Alder reactionTetrahedron: Asymmetry, 2005