Rigid P-Chiral Phosphorus Ligands for Highly Selective Palladium-Catalyzed (4+2) and (4+4) Annulations
- 12 December 2022
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 24 (50) , 9205-9209
Abstract
We developed novel shackled P-chiral ligands based on 1-phosphanorbornenes and oxazolines. They were subsequently evaluated in palladium-catalyzed (4+2) annulations, producing enantioenriched tetrahydropyran scaffolds in good yields with high site selectivity and enantioselectivity. Moreover, chemoselective (4+4) products were also achieved by using acyclic imines. In addition, density functional theory calculations were performed to afford the energy profile of the Michael addition step and ring formation step. This demonstrated that the enantioselective (4+2) annulations and the chemoselective reaction between (4+2) and (4+4) products were mostly under thermodynamic control.Keywords
Funding Information
- Zhengzhou University (JC21253007)
- China Postdoctoral Science Foundation (2022M722865)
- National Natural Science Foundation of China (21672193, 21702189, 22101266, 22171245)
- Henan Province (202102310004)
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