TY - JOUR
T1 - Synthesis of Functionalized Tetrasubstituted Allenes by the Addition of Bis(trimethylsilyl)ketene Acetals to Ynones Catalyzed by Gold(I)
AU - Rosales-Amezcua, Saulo C.
AU - Ballinas-Indili, Ricardo
AU - López-Reyes, Morelia E.
AU - Guevara-Vela, José Manuel
AU - Rocha-Rinza, Tomás
AU - Toscano, Rúben A.
AU - Álvarez-Toledano, Cecilio
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/3/1
Y1 - 2024/3/1
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/85185595397
U2 - 10.1021/acs.joc.3c02550
DO - 10.1021/acs.joc.3c02550
M3 - Article
C2 - 38359145
AN - SCOPUS:85185595397
SN - 0022-3263
VL - 89
SP - 3092
EP - 3101
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -