期刊
ORGANIC LETTERS
卷 17, 期 24, 页码 6254-6257出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b03265
关键词
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资金
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [NRF-2015R1A5A1008958]
- National Research Foundation of Korea [2015R1A5A1008958] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
The eliminative reaction pathways of (E)-beta-chlorovinyl ketones were investigated in the presence of both Bronsted and Lewis bases. The Bronsted base, Et3N, effected the soft alpha-vinyl enolization of (E)-beta-chlorovinyl ketones to [3]cumulenol intermediates; in turn, a catalytic amount of Lewis base, PPh3, initiated isomerization to provide 1,3-dienones in high yields. The introduction of a carbon-based nucleophile into the reaction mixture provided the highly efficient synthetic route to 2H-pyran-2-ones in one pot, where the carbon-based nucleophile generated by an extra equivalent of Bronsted base, Et3N, attacked the electrophilic [3]cumulenol intermediates to initiate cyclization to give 2H-pyran-2-ones.
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