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
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Sprache:eng
Schlagworte:
migratory behavior
odor compounds
organic chemistry
reaction mechanisms
sensory evaluation
X-radiation
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container_end_page 5297
container_issue 8
container_start_page 5287
container_title Journal of organic chemistry
container_volume 89
creator Zeng, Huiyi
Ye, Zihao
Chai, An
Jiang, You
Zou, Yue
Wu, Fanhong
Li, Zhiming
Zhou, Lijun
description 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.
doi_str_mv 10.1021/acs.joc.3c02645
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source ACS Publications
subjects migratory behavior
odor compounds
organic chemistry
reaction mechanisms
sensory evaluation
X-radiation
title Direct Oxidative Cyclization of 3‑Arylpropionic Acids to 3,4-Dihydrocoumarins: Reinvestigation of the Reaction Mechanism
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