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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Chiral amplification based on enantioselective dual-phase distribution of a scalemic bisoxazolidine catalyst
Shuanglong Liu1, Christian Wolf
1Department of Chemistry, Georgetown University, Washington, DC 20057, USA.
Abstract:
A readily available bisoxazolidine ligand was found to catalyze the asymmetric alkylation of aldehydes with Et(2)Zn and less reactive Me(2)Zn, 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 ML(n) 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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