A1 Journal article (refereed)
Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael-Domino Michael/Aldol Reaction (2022)


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


JYU authors or editors


Publication details

All authors or editors: Straminelli, Leonardo; Vicentini, Francesco; Di Sabato, Antonio; Montone, Carmela Maria; Cavaliere, Chiara; Rissanen, Kari; Leonelli, Francesca; Vetica, Fabrizio

Journal or series: Journal of Organic Chemistry

ISSN: 0022-3263

eISSN: 1520-6904

Publication year: 2022

Publication date: 25/07/2022

Volume: 87

Issue number: 15

Pages range: 10454-10461

Publisher: American Chemical Society (ACS)

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.joc.2c01046

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/82754


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).


Keywords: organic chemistry; chemical synthesis


Contributing organizations


Ministry reporting: Yes

Reporting Year: 2022

Preliminary JUFO rating: 2


Last updated on 2022-20-09 at 13:14