1,3-Dienones and 2H-Pyran-2-ones from Soft α-Vinyl Enolization of β-Chlorovinyl Ketones: Defined Roles of Brönsted and Lewis Base
作者： Hun Young Kim , Kyungsoo Oh
DOI: 10.1021/ACS.ORGLETT.5B03265
关键词: Keto–enol tautomerism 、 Catalysis 、 Nucleophile 、 Isomerization 、 Electrophile 、 Chemistry 、 Lewis acids and bases 、 Pyran 、 Brønsted–Lowry acid–base theory 、 Medicinal chemistry 、 Organic chemistry
摘要: The eliminative reaction pathways of (E)-β-chlorovinyl ketones were investigated in the presence both Bronsted and Lewis bases. base, Et3N, effected soft α-vinyl enolization to [3]cumulenol intermediates; turn, a catalytic amount PPh3, initiated isomerization provide 1,3-dienones high yields. introduction carbon-based nucleophile into mixture provided highly efficient synthetic route 2H-pyran-2-ones one pot, where generated by an extra equivalent attacked electrophilic intermediates initiate cyclization give 2H-pyran-2-ones.
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