Direct Oxidative Cyclization of 3‑Arylpropionic Acids to 3,4-Dihydrocoumarins: Reinvestigation of the Reaction Mechanism

Direct Oxidative Cyclization of 3‑Arylpropionic Acids to 3,4-Dihydrocoumarins: Reinvestigation of the Reaction Mechanism

Instigated by olfactory analysis of odorant molecules, the constitutions of 3,4-dihydrocoumarins prepared by PIFA-based oxidative cyclizations of 3-arylpropionic acids were revised by means of 2D NMR and X-ray analysis. Supported by computational analysis, the migratory mechanism of intermediate spi...

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Veröffentlicht in:Journal of organic chemistry 2024-04, Vol.89 (8), p.5287-5297
Hauptverfasser: Zeng, Huiyi, Ye, Zihao, Chai, An, Jiang, You, Zou, Yue, Wu, Fanhong, Li, Zhiming, Zhou, Lijun
Format: Artikel
Sprache:eng
Schlagworte:
migratory behavior
odor compounds
organic chemistry
reaction mechanisms
sensory evaluation
X-radiation
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Zusammenfassung:Instigated by olfactory analysis of odorant molecules, the constitutions of 3,4-dihydrocoumarins prepared by PIFA-based oxidative cyclizations of 3-arylpropionic acids were revised by means of 2D NMR and X-ray analysis. Supported by computational analysis, the migratory mechanism of intermediate spirolactonic cations has been amended: 1,2-alkyl shifts instead of 1,2-carboxylic shifts were selectively obtained.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c02645