Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction

[Image: see text] A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a high...

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Detalles Bibliográficos
Autores principales: Straminelli, Leonardo, Vicentini, Francesco, Di Sabato, Antonio, Montone, Carmela Maria, Cavaliere, Chiara, Rissanen, Kari, Leonelli, Francesca, Vetica, Fabrizio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9365295/
https://www.ncbi.nlm.nih.gov/pubmed/35875873
http://dx.doi.org/10.1021/acs.joc.2c01046
Descripción
Sumario:[Image: see text] A highly stereoselective procedure for the synthesis of spiro-polycyclic oxindoles bearing five contiguous stereogenic centers including two tetrasubstituted carbons has been developed. Under sequential organocatalysis performed by a pyrrolidine-based organocatalyst and DBU, a highly atom-economical Michael–domino Michael/aldol reaction sequence was optimized, yielding variously functionalized spiro-decalin oxindoles with excellent stereoselectivity (>99:1 dr, up to 92% ee).

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