Cu(I)-catalyzed asymmetric allylation of ketones and ketimines

Cu(I)-catalyzed asymmetric allylation of ketones and ketimines

Chiral CuF-catalyzed asymmetric allylation of ketones and ketimines is described. Nucleophile activation via transmetallation (allylboronate to allylcopper), which is facilitated by a cocatalyst [La(O Pr) or LiO Pr], is key for these reactions. A CuOTf-3KO Bu-DUPHOS complex is a comparably effective...

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Veröffentlicht in:Pure and applied chemistry 2008-05, Vol.80 (5), p.1055-1062
Hauptverfasser: Kanai, Motomu, Wada, Reiko, Shibuguchi, Tomoyuki, Shibasaki, Masakatsu
Format: Artikel
Sprache:eng
Schlagworte:
Allyl compounds
allylation
asymmetric catalysis
Chemical reactions
copper
Imines
ketimines
Ketones
Phosphines
tetrasubstituted carbon
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Zusammenfassung:Chiral CuF-catalyzed asymmetric allylation of ketones and ketimines is described. Nucleophile activation via transmetallation (allylboronate to allylcopper), which is facilitated by a cocatalyst [La(O Pr) or LiO Pr], is key for these reactions. A CuOTf-3KO Bu-DUPHOS complex is a comparably effective catalyst that reduces the required amount of chiral phosphines.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200880051055