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

Leonardo Straminelli
Co-primo
;
Francesco Vicentini
Co-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).
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11573/1651295
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