Copper-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Imino Esters to Unsaturated Sultones
Shohei Furuya1, Kazuya Kanemoto1, Shin-Ichi Fukuzawa1
1Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
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.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Related Concept Videos
Cycloaddition Reactions: Overview
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Preparation and Reactions of Sulfides
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
