ProPhenol Derived Ligands to Simultaneously Coordinate a Main-Group Metal and a Transition Metal: Application to a Zn−Cu Catalyzed Reaction |
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| Authors: | Prof Dr Barry M Trost Dr Guoting Zhang Minghao Xu Prof Dr Xiaotian Qi |
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| Institution: | 1. Department of Chemistry, Stanford University, Stanford, California, 94035-5080 United States;2. Department College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China |
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| Abstract: | A new bifunctional ligand bearing chiral N-heterocyclic carbene (NHC) and prolinol moieties is presented. Utilizing the designed ligand, an in situ formed Cu/Zn hetero-bimetallic complex unlocks the asymmetric allylic alkylation reactions of allyl phosphates with zinc keto-homoenolates, leading to the formation of various γ-vinyl ketones with good regio- and enantio-selectivity. DF sT calculation supports that the chelation of allyl phosphates with catalyst promotes the SN2’ addition and the ligand-substrate steric interactions account for the stereoselective outcome. |
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| Keywords: | asymmetric catalysis bimetallic catalysis C−C bond formation |
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