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Synthesis 2012; 44(21): 3307-3314
DOI: 10.1055/s-0032-1316779
DOI: 10.1055/s-0032-1316779
paper
Asymmetric [3+2] Cycloaddition of Azomethine Ylides Catalyzed by Silver(I) Triflate with a Chiral Bipyrrolidine-Derived Phosphine Ligand
Further Information
Publication History
Received: 26 June 2012
Accepted after revision: 30 August 2012
Publication Date:
14 September 2012 (online)
Abstract
Two novel chiral bipyrrolidine-derived phosphine ligands L1 and L2 were synthesized. The ‘AgOTf + L1’ protocol catalyzes the asymmetric [3+2] cycloaddition of azomethine ylides with alkenes to give highly substituted pyrrolidines in good yields (up to 90%) with moderate to high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 76%).
Key words
asymmetric [3+2] cycloaddition - silver catalysis - azomethine ylides - chiral phosphine ligand - highly substituted pyrrolinesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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Reviews on transition-metal-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
Selected examples on transition-metal-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
Reviews on silver-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
Selected examples on silver-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with alkenes:
Reviews: