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 in | Journal of organic chemistry Vol. 89; no. 5; pp. 3092 - 3101 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
01.03.2024
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| Abstract | 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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| AbstractList | 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. 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. |
| Author | López-Reyes, Morelia E. Álvarez-Toledano, Cecilio Rocha-Rinza, Tomás Rosales-Amezcua, Saulo C. Ballinas-Indili, Ricardo Guevara-Vela, José Manuel Toscano, Rúben A. |
| AuthorAffiliation | Departamento de Química Física Aplicada Instituto de Química Universidad Autónoma de Madrid Universidad de Guadalajara Departamento de Química |
| AuthorAffiliation_xml | – name: Universidad de Guadalajara – name: Universidad Autónoma de Madrid – name: Instituto de Química – name: Departamento de Química Física Aplicada – name: Departamento de Química |
| Author_xml | – sequence: 1 givenname: Saulo C. surname: Rosales-Amezcua fullname: Rosales-Amezcua, Saulo C. organization: Instituto de Química – sequence: 2 givenname: Ricardo surname: Ballinas-Indili fullname: Ballinas-Indili, Ricardo email: ricardoballinas1989@gmail.com organization: Instituto de Química – sequence: 3 givenname: Morelia E. orcidid: 0000-0002-1311-7553 surname: López-Reyes fullname: López-Reyes, Morelia E. email: morelia.lopez@academicos.udg.mx organization: Universidad de Guadalajara – sequence: 4 givenname: José Manuel surname: Guevara-Vela fullname: Guevara-Vela, José Manuel organization: Universidad Autónoma de Madrid – sequence: 5 givenname: Tomás surname: Rocha-Rinza fullname: Rocha-Rinza, Tomás organization: Instituto de Química – sequence: 6 givenname: Rúben A. surname: Toscano fullname: Toscano, Rúben A. organization: Instituto de Química – sequence: 7 givenname: Cecilio surname: Álvarez-Toledano fullname: Álvarez-Toledano, Cecilio email: cecilio@unam.mx organization: Instituto de Química |
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| Snippet | We have developed a straightforward and rapid methodology for the synthesis of tetrasubstituted allenes bearing carboxylic acids in the 1,3-position through... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Synthesis of Functionalized Tetrasubstituted Allenes by the Addition of Bis(trimethylsilyl)ketene Acetals to Ynones Catalyzed by Gold(I) |
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