Recent progress in the application of fluorinated chiral sulfinimine reagents

Application of fluorinated chiral sulfinimine reagents, in particularly, N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine, as electrophiles for the synthesis of compounds bearing fluoro-amino-keto/hydroxy moieties have been summarized. [Display omitted] •Recent advances in the asymmetric reactions o...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of fluorine chemistry 2018-12, Vol.216, p.57-70
Hauptverfasser: Mei, Haibo, Han, Jianlin, Fustero, Santos, Román, Raquel, Ruzziconi, Renzo, Soloshonok, Vadim A.
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Application of fluorinated chiral sulfinimine reagents, in particularly, N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine, as electrophiles for the synthesis of compounds bearing fluoro-amino-keto/hydroxy moieties have been summarized. [Display omitted] •Recent advances in the asymmetric reactions of chiral fluorinated sulfinimine reagents were presented.•Several types of fluorinated imines were profiled.•The discussed methods provide a general approach for preparation of compounds containing pharmacophoric fluoro-amino- keto/hydroxy moieties. The development of synthetic methodology allowing for a strategic incorporation of fluorine into target compounds is in a high demand in many areas of the chemical and pharmaceutical industries. In this regard, application of fluorinated chiral sulfinimine reagents, in particularly, N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine, is one of the most general and practical approaches for preparation of compounds containing pharmacophoric fluoro-amino-keto/hydroxy moieties. This article provides a timely and comprehensive overview of the recent synthetic applications of fluorinated chiral sulfinimine reagents for asymmetric synthesis of fluoro-containing polyfunctional amino-compounds of biological interest. Where it is possible, we emphasize the synthetic versatility and practicality of the reported methods.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2018.10.003