Sebastijan Ričko (Author), Žan Testen (Author), Luka Ciber (Author), Franc Požgan (Author), Bogdan Štefane (Author), Helena Brodnik Žugelj (Author), Jurij Svete (Author), Uroš Grošelj (Author)

Abstract

Arylidene-∆$^2$-pyrrolin-4-ones undergo organocatalyzed double spirocyclization with 3-isothiocianato oxindoles in a domino 1,4/1,2-addition sequence. The products contain three contiguous stereocenters (ee up to 98%, dr up to 99:1, 12 examples). The absolute configuration of the major diastereomer was determined by single crystal X-ray analysis. Along with heterocyclic Michael acceptors based on oxazolone, isoxazolone, thiazolidinone, pyrazolone, and pyrimidinedione, the reported results display the applicability of unsaturated ∆$^2$-pyrrolin-4-ones (pyrrolones) for the organocatalyzed construction of 3D-rich pyrrolone-containing heterocycles.

Keywords

organokatalizatorji;piroloni;spiroheterociklizacija;3-izotiocianato oksindoli;kaskadne reakcije;spiro spojine;organocatalysis;pyrrolones;spiroheterocyclization;3-isothiocyanato oxindoles;cascade reaction;spiro compounds;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.74
COBISS: 33665795 Link will open in a new window
ISSN: 2073-4344
Views: 153
Downloads: 46
Average score: 0 (0 votes)
Metadata: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Other data

Secondary language: Slovenian
Secondary keywords: organokatalizatorji;piroloni;spiroheterociklizacija;3-izotiocianato oksindoli;kaskadne reakcije;spiro spojine;
Type (COBISS): Article
Pages: str. 1-13
Volume: ǂVol. ǂ10
Issue: ǂiss. ǂ10
Chronology: Oct. 2020
DOI: 10.3390/catal10101211
ID: 14373111