Iridium-Catalyzed, Highly Selective Allylation of Pyrazolones for the Convenient Construction of Adjacent Stereocenters
This paper describes an iridium-catalyzed allylation of ring-fused pyrazolones that proceeds with excellent regio-, diastereo- and enantio-selectivities. The approach exploits unactivated, racemic allylic alcohols as a source of allyl building blocks. Asymmetric syntheses of a series of biologically relevant, chiral pyrazolones highlight the utility of the methodology. The use of Cu(OTf)<sub>2</sub> as a co-catalyst greatly enhances the regioselectivity of the reaction and permits selective syntheses of branched allylation products.
Authors
- Martin G. Banwell (ORCID: https://orcid.org/0000-0002-0582-475X)
- Leijie Zhou (ORCID: https://orcid.org/0000-0001-8245-8178)
- Shixiang Sun (ORCID: https://orcid.org/0000-0001-5499-2963)
- Lorenzo V. White (ORCID: https://orcid.org/0000-0002-6450-3761)
- Yuqi Zhang (ORCID: https://orcid.org/0000-0001-9577-3150)
Institutions
- Jinan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-22
- DOI
- https://doi.org/10.1021/acs.orglett.4c03586
- Citations
- 3
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Guangzhou Municipal Science and Technology Project
- Science and Technology Planning Project of Guangdong Province
- Basic and Applied Basic Research Foundation of Guangdong Province