期刊
ACS CATALYSIS
卷 10, 期 9, 页码 5335-5346出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01413
关键词
photocatalysis; enantioselective [2+2] photocycloaddition; iminium ion catalysis; charge transfer complex; EDA complex photoactivity; cyclobutanes; aminocatalysis
资金
- European Research Council (ERC-CoG) [647550]
- Spanish Government [RTI2018-095038-B-I00]
- Comunidad de Madrid
- European Structural Funds [S2018/NMT-4367]
An asymmetric aminocatalytic activation strategy to obtain enantioenriched cyclobutanes through [2 + 2] photo-cycloaddition under visible light irradiation is presented. This metal-free process does not require the use of any external photocatalyst, as it is catalyzed by a simple diamine which, upon condensation with an enone substrate, forms an iminium ion intermediate that absorbs in the visible light region. The direct excitation of such an intermediate leads to a charge transfer (CT) excited state that unlocks a stereocontrolled intermolecular photocycloaddition with good enantiomeric and diastereoisomeric ratios and high yields. Finally, DFT calculations and experiments were performed to support the charge transfer behavior and the mechanistic proposal.
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