Enantioselective Copper-Catalyzed 1, 4-Addition of Dialkylzincs to Enones Followed by Trapping with Allyl Iodide Derivatives

K Kawamura, H Fukuzawa, M Hayashi

Index: Kawamura, Kenjiro; Fukuzawa, Hitomi; Hayashi, Masahiko Bulletin of the Chemical Society of Japan, 2011 , vol. 84, # 6 p. 640 - 647

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Citation Number: 10

Abstract

Enantioselective copper-catalyzed 1, 4-addition of dialkylzincs to enones proceeded in the presence of 0.1 mol% of Cu (OTf) 2 and 0.25 mol% of an N, N, P-ligand containing a quinoline moiety to afford the corresponding conjugated adducts in 99% ee. The intermediate zinc enolates were trapped with substituted allyl iodides to give disubstituted ketones with high diastereoselectivity and enantioselectivity.