研究目的
To exploit the photochemical activity of chiral iminium ions to activate allenes by SET oxidation and design a cascade process leading to complex, polysubstituted bicyclic lactones.
研究成果
The study successfully exploited the photochemical activity of chiral iminium ions to activate allenes by SET oxidation, leading to complex, polysubstituted bicyclic lactones with good enantioselectivity and exquisite diastereoselectivity. This activation strategy offers new opportunities to expand the synthetic potential of allenes.
研究不足
Aliphatic enals were not suitable substrates as reactivity was completely inhibited. The system's scope is limited by the unique reactivity of allene cation radicals.
1：Experimental Design and Method Selection:
The study employs a visible light-driven enantioselective organocatalytic process using the excited-state reactivity of chiral iminium ions to activate allenes by SET oxidation.
2：Sample Selection and Data Sources:
Allenic acid 1a was selected as the model substrate due to its oxidation potential.
3：List of Experimental Equipment and Materials:
A Schlenk flask, high-power LED (λmax = 420 nm), Zn(OTf)2, CH3CN, and a chiral amine catalyst were used.
4：Experimental Procedures and Operational Workflow:
The reaction was performed in CH3CN under irradiation by a single high-power LED, with the mixture degassed and kept under an atmosphere of argon.
5：Data Analysis Methods:
The enantiomeric excess was determined by UPC2 analysis on a chiral stationary phase.
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