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The first direct evidence was found on the interaction of the lone pair of the quinuclidine N atom and the prochiral keto-carbonyl group of the KPL. Strong n(N) -> pi* interactions were observed between the nonbonding orbital of the quinuclidine N atom and the pi* antibonding orbitals of the C=O bonds. The complex was demonstrated experimentally to be stabilized not only by the H bonds between H5' of the chiral modifier and the KPL, but also, depending on the structure of the cinchona alkaloid, by those between H8 and H9 and the KPL. In aprotic solvents, this type of experimentally verified adduct may be present on the Pt surface and participate in chiral induction in the Orito reaction. (c) 2006 Elsevier Inc. 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