Synthesis of Functionalized Tetrasubstituted Allenes by the Addition of Bis(trimethylsilyl)ketene Acetals to Ynones Catalyzed by Gold(I)

We have developed a straightforward and rapid methodology for the synthesis of tetrasubstituted allenes bearing carboxylic acids in the 1,3-position through the gold­(I)-catalyzed nucleophilic addition of bis­(trimethylsilyl)­ketene acetals to ynones. The reaction was evaluated with several substrat...

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Published inJournal of organic chemistry Vol. 89; no. 5; pp. 3092 - 3101
Main Authors Rosales-Amezcua, Saulo C., Ballinas-Indili, Ricardo, López-Reyes, Morelia E., Guevara-Vela, José Manuel, Rocha-Rinza, Tomás, Toscano, Rúben A., Álvarez-Toledano, Cecilio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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DESIGN
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Summary:We have developed a straightforward and rapid methodology for the synthesis of tetrasubstituted allenes bearing carboxylic acids in the 1,3-position through the gold­(I)-catalyzed nucleophilic addition of bis­(trimethylsilyl)­ketene acetals to ynones. The reaction was evaluated with several substrates, and 21 allenes were obtained in moderate to good yields. Using DFT calculations, we studied the mechanism of the reaction, which suggested a nucleophilic 1,4-addition pathway. The potential of allenes to act as a source of highly functionalized lactones was also explored.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c02550