Enantioselective Synthesis of Benzothiazolines from Fluoroalkyl Ketones Using Chiral Imidazoline−Phosphoric Acid Catalysts

The first enantioselective synthesis of cyclic N,S‐ketals having tetrasubstituted chiral center through intramolecular cyclization between carbonyl compounds and aminothiols has been developed. The reaction of fluoroalkyl ketones with aminobenzenethiols using a chiral imidazoline−phosphoric acid cat...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Advanced synthesis & catalysis 2022-12, Vol.364 (24), p.4271-4274
Hauptverfasser: Iizuka, Yuka, Wada, Tatsumi, Ogura, Kazuki, Takehara, Tsunayoshi, Suzuki, Takeyuki, Nakamura, Shuichi
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The first enantioselective synthesis of cyclic N,S‐ketals having tetrasubstituted chiral center through intramolecular cyclization between carbonyl compounds and aminothiols has been developed. The reaction of fluoroalkyl ketones with aminobenzenethiols using a chiral imidazoline−phosphoric acid catalyst afforded products in high yields with high enantioselectivity. The observed enantioselectivity is explained using preliminary mechanistic information.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202201039