Asymmetric Ni-Catalyzed Conjugate Allylation of Activated Enones

The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The reaction appears to proceed by conversion of the...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of the American Chemical Society 2008-04, Vol.130 (14), p.4978-4983
Hauptverfasser:	Sieber, Joshua D, Morken, James P
Format:	Artikel
Sprache:	eng
Schlagworte:	Allyl Compounds - chemistry Boronic Acids - chemistry Catalysis Ketones - chemistry Magnetic Resonance Spectroscopy Nickel - chemistry Stereoisomerism
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The reaction appears to proceed by conversion of the dialkylidene ketone substrate to an unsaturated π-allyl complex (I), followed by reductive elimination. Enantioselectivities range from 91 to 94% ee for a range of substrates when chiral ligand 14 is employed.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja710922h