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

doi:10.1021/acs.joc.2c01046

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Straminelli, L., Vicentini, F., Di Sabato, A., Montone, C. M., Cavaliere, C., Rissanen, K., Leonelli, F., & Vetica, F. (2022). Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction. Journal of Organic Chemistry, 87(15), 10454-10461. https://doi.org/10.1021/acs.joc.2c01046

Julkaistu sarjassa

Journal of Organic Chemistry

Tekijät

Straminelli, Leonardo |

Vicentini, Francesco |

Di Sabato, Antonio |

Montone, Carmela Maria |

Cavaliere, Chiara |

Rissanen, Kari |

Leonelli, Francesca |

Vetica, Fabrizio

Päivämäärä

2022

Oppiaine

Orgaaninen kemia Organic Chemistry

Tekijänoikeudet

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).

Julkaisija

American Chemical Society (ACS)

ISSN Hae Julkaisufoorumista

0022-3263

Lisätietoja rahoituksesta

The authors gratefully thank the colleagues at Sapienza University of Rome (Prof. Patrizia Gentili, Prof. Marta Feroci, Prof. Marco Bella), Dr. Giuliana Righi, and the Institute of Biological Systems (ISB) of the Italian National Research Council (CNR) for the donation of chemicals. Financial support from Sapienza University of Rome (Grant Number RP12117A5C0CA0CC) is gratefully acknowledged.

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