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A readily available bisoxazolidine ligand was found to catalyze the asymmetric alkylation of aldehydes with Et2Zn and less reactive Me2Zn, providing high yields and ee’s in both reactions. The bisoxazolidine-catalyzed alkylations and alkynylation of benzaldehyde show a positive nonlinear effect that cannot be accounted for by Kagan’s MLn model. The chiral amplification originates from selective phase distribution favoring enrichment of the major enantiomer of the scalemic catalyst in solution.
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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis