Base-Promoted 5-exo-dig Cyclization of o‑Alkynylamides or 2‑En-4-ynamides with CO2 toward Fully Substituted Acrylates

A base-promoted sequential cyclization and carboxylation of o-alkynylamides or 2-en-4-ynamides with CO2 has been achieved with high efficiency, stereoselectivity, and regioselectivity. This approach begins with 5-exo-dig cyclization followed by trapping the resulting vinyl anion with CO2 and MeI, wh...

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Veröffentlicht in:Organic letters 2022-08, Vol.24 (31), p.5715-5720
Hauptverfasser: Sha, Yu, Bai, Junxue, Li, Miao, Gao, Wanxu, Yang, Qi, Sun, Jianwei, Sun, Song
Format: Artikel
Sprache:eng
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Zusammenfassung:A base-promoted sequential cyclization and carboxylation of o-alkynylamides or 2-en-4-ynamides with CO2 has been achieved with high efficiency, stereoselectivity, and regioselectivity. This approach begins with 5-exo-dig cyclization followed by trapping the resulting vinyl anion with CO2 and MeI, which provides a convenient access to diverse cyclic and fully substituted acrylates with CO2 as the carboxylic source.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02123