Cerium (III) chloride mediated nitrile aldol reactions: Enhanced diastereoselectivities using a chiral organocerium complex

Z Xiao, JW Timberlake

Index: Xiao, Zejun; Timberlake, Jack W. Tetrahedron, 1998 , vol. 54, # 17 p. 4211 - 4222

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Citation Number: 19

Abstract

The addition of anhydrous cerium chloride to nitrile aldol reactions has been found to provide high yields of β-hydroxynitriles. Also, the aldol reaction of α, β-unsaturated carbonyl compounds with nitrile enolates in the presence of cerium chloride affords 1, 2 addition exclusively in good to excellent yields. The organocerium complexes of R-(+)-1, 1′-bi-2- naphthol have successfully mediated the aldol addition of lithio alkyl and arylacetonitriles ...