Asymmetric Syntheses of 1-Aryl-2,2,2-trifluoroethylamines via Diastereoselective 1,2-Addition of Arylmetals to 2-Methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide

Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a−g....

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2007-02, Vol.9 (4), p.683-685
Hauptverfasser:	Truong, Vouy Linh, Ménard, Madelaine S, Dion, Isabelle
Format:	Artikel
Sprache:	eng
Schlagworte:	Chromatography, High Pressure Liquid Ethylamines - chemical synthesis Hydrocarbons, Fluorinated - chemical synthesis Hydrocarbons, Fluorinated - chemistry Imines - chemical synthesis Indicators and Reagents Organometallic Compounds - chemistry Stereoisomerism Sulfonium Compounds - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Condensation of N-tert-butanesulfinamide (S)-1 with trifluoroacetaldehyde hydrate 2a afforded 2-methyl-N-(2,2,2-trifluoroethylidene)propane-2-sulfinamide 3. Without isolation and purification, imine 3 was added to various aryllithium reagents to give highly diastereomerically enriched adducts 5a−g. Acidic methanolysis of 5a−g provided the desired 1-aryl-2,2,2-trifluoroethylamine hydrochloride compounds 6a−g.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol063001q