Asymmetric Synthesis of Spiropyrazolones via Chiral Pd(0)/Ligand Complex-Catalyzed Formal [4+2] Cycloaddition of Vinyl Benzoxazinanones with Alkylidene Pyrazolones
- 30 December 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 86 (2), 1712-1720
- https://doi.org/10.1021/acs.joc.0c02524
Abstract
In the presence of the chiral Pd(0)/ligand complex, vinyl benzoxazinanones underwent the [4+2] cycloaddition with alkylidene pyrazolones smoothly and delivered spiropyrazolones in reasonable yields, diastereoselectivities, and eneantioselectivities (up to >99% yield, >99:1 dr and 99% ee). The absolute configuration of the obtained spiropyrazolones was unambiguously characterized with the use of X-ray single-crystal structure analysis. Moreover, the reaction mechanism was assumed to interpret the formation of the target compounds.Keywords
Funding Information
- Beijing Municipal Commission of Education (JC015001200902)
- Funding Project for Academic Human Resources Development in Institutions of Higher Learning under the Jurisdiction of Beijing Municipality (PHR201008025)
- Doctoral Scientific Research Start-up Foundation of Beijing University of Technology (52015001200701)
- Basic Research Foundation of Beijing University of Technology (X4015001201101)
- Beijing Natural Science Foundation (7102010;2122008;2172003)
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