Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols

Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols

Giving it a boost: A mechanistic study of the enantioselective asymmetric titled reaction with allyldiisopropoxyborane catalyzed by chiral biphenols revealed a key ligand exchange process which liberates isopropyl alcohol. The addition of iPrOH to the reaction increases the overall rate and enantios...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (46), p.8679-8682
Hauptverfasser: Barnett, David S, Moquist, Philip N, Schaus, Scott E
Format: Artikel
Sprache:eng
Schlagworte:
Boranes - chemical synthesis
Boranes - chemistry
boron
Catalysis
homogeneous catalysis
Isomerism
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Phenols - chemistry
reaction mechanisms
synthetic methods
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Giving it a boost: A mechanistic study of the enantioselective asymmetric titled reaction with allyldiisopropoxyborane catalyzed by chiral biphenols revealed a key ligand exchange process which liberates isopropyl alcohol. The addition of iPrOH to the reaction increases the overall rate and enantioselectivity. As a result an improved reaction, employing allyldioxaborinane with 1 and tBuOH, resulted in high product yields and enantioselectivities.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904715