Enantioselective synthesis of spiroimidazolones by synergistic catalysis

The present study investigates an enantioselective cyclization of enals with imidazolone derivatives catalyzed by a combination of achiral Pd(0) complex and chiral secondary amine. Corresponding spirocyclic imidazolones were produced in high yields with moderate diastereoselectivity and excellent en...

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Veröffentlicht in:Catalysis today 2024-02, Vol.428, p.114443, Article 114443
Hauptverfasser: Franc, Michael, Císařová, Ivana, Veselý, Jan
Format: Artikel
Sprache:eng
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Zusammenfassung:The present study investigates an enantioselective cyclization of enals with imidazolone derivatives catalyzed by a combination of achiral Pd(0) complex and chiral secondary amine. Corresponding spirocyclic imidazolones were produced in high yields with moderate diastereoselectivity and excellent enantioselectivity. The developed co-operative catalytic methodology provides a highly substituted spirocyclic scaffold with four stereogenic centers under mild conditions. [Display omitted] •Synergistically catalyzed reaction leading to spirocyclic compounds.•Combination of chiral secondary amine and achiral palladium complex as catalysts.•Preparation of a wide variety of chiral spiroimidazolones.•Readily derivatization of prepared chiral spiroimidazolones.
ISSN:0920-5861
1873-4308
DOI:10.1016/j.cattod.2023.114443