Asymmetric Conjugate Reductions of Coumarins. A New Route to Tolterodine and Related Coumarin Derivatives

The combination of catalytic amounts of [(R)-DTBM-SEGPHOS]CuH in the presence of stoichiometric DEMS (diethoxymethylsilane) in toluene at room temperature leads to asymmetric reductions of 4-substituted coumarins. Several targets or their known precursors can be prepared in high yields and ee’s, inc...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2009-12, Vol.11 (23), p.5374-5377
Hauptverfasser:	Gallagher, Brian D, Taft, Benjamin R, Lipshutz, Bruce H
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzhydryl Compounds - chemical synthesis Benzhydryl Compounds - chemistry Benzhydryl Compounds - pharmacology Catalysis Coumarins - chemical synthesis Coumarins - chemistry Coumarins - pharmacology Cresols - chemical synthesis Cresols - chemistry Cresols - pharmacology Cyclization Oxidation-Reduction Phenylpropanolamine - chemical synthesis Phenylpropanolamine - chemistry Phenylpropanolamine - pharmacology Receptors, G-Protein-Coupled - agonists Stereoisomerism Tolterodine Tartrate
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The combination of catalytic amounts of [(R)-DTBM-SEGPHOS]CuH in the presence of stoichiometric DEMS (diethoxymethylsilane) in toluene at room temperature leads to asymmetric reductions of 4-substituted coumarins. Several targets or their known precursors can be prepared in high yields and ee’s, including the muscarine receptor antagonist (R)-tolterodine.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol9020404