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).
Stereoselective synthesis of spiro-decalin oxindole derivatives via sequential organocatalytic Michael–domino Michael/aldol reaction / Straminelli, Leonardo; Vicentini, Francesco; DI SABATO, Antonio; Montone, CARMELA MARIA; Cavaliere, Chiara; Rissanen, Kari; Leonelli, Francesca; Vetica, Fabrizio. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 87:15(2022), pp. 10454-10461. [10.1021/acs.joc.2c01046]
Stereoselective synthesis of spiro-decalin oxindole derivatives via sequential organocatalytic Michael–domino Michael/aldol reaction
Leonardo StraminelliCo-primo
;Francesco VicentiniCo-primo
;Antonio Di Sabato;Carmela Maria Montone;Chiara Cavaliere;Francesca Leonelli;Fabrizio Vetica
2022
Abstract
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).| File | Dimensione | Formato | |
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