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Studies of chiral Lewis acid catalyzed enantioselective reactions using strongly coordinating nucleophiles, as a rather unexplored categoly of catalyzed enantioselective reactions, are described. Selection of a proper chiral catalyst should be essential. The author has employed complexes of two chiral ligands, (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) and (R,R)-isopropylidene-2,2'-bis[4-(o-hydroxybenzyl)oxazoline)], designated R,RDBFOX/Ph and R,R-BOX/o-HOBn, respectively. The complex catalyst derived from R,R-DBFOX/Ph and Ni(ClO4)2 . 3H2O works as a powerful catalyst in the enantioselective thiol conjugate additions to 3-(2-alkenoyl)-2-oxazolines, and the complex derived from R,R-BOX/o-HOBn and Cu(OTf)2 catalyzes the reactions of O-benzylhydroxylamine to 1-alkyl-3-(2-alkenoyl)-2-imidazolidinones. Internal delivery of nucleophiles to the activated acceptors is proposed as a powerful principle for the development of the titled reactions

proceedings of the 4th international electronic conference on synthetic organic chemistry

Lewis Acid Catalyzed Enantioselective Reactions Using Highly Coordinating Nucleophiles. Conjugate Additions of Thiols, Thiocarboxylic acids, and O-Benzylhydroxylamine