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 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).
2022
asymmetric organocatalysis; oxindoles; sprio heterocycles; domino reactions
01 Pubblicazione su rivista::01a Articolo in rivista
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]
File allegati a questo prodotto
File Dimensione Formato  
Straminelli_ Stereoselective_2022.pdf

accesso aperto

Tipologia: Versione editoriale (versione pubblicata con il layout dell'editore)
Licenza: Creative commons
Dimensione 1.75 MB
Formato Adobe PDF
1.75 MB Adobe PDF

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1651295
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 4
  • ???jsp.display-item.citation.isi??? 4
social impact