Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction.
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). peerReviewed
CCDC 2165719: Experimental Crystal Structure Determination
Related Article: Leonardo Straminelli, Francesco Vicentini, Antonio Di Sabato, Carmela Maria Montone, Chiara Cavaliere, Kari Rissanen, Francesca Leonelli, Fabrizio Vetica|2022|J.Org.Chem.|87|10454|doi:10.1021/acs.joc.2c01046