Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 9, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202104268
Keywords
asymmetric catalysis; bimetallic catalysis; C-C bond formation
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Funding
- Tamaki Foundation
- Chugai Pharmaceutical
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A new bifunctional ligand with chiral NHC and prolinol moieties was introduced for asymmetric allylic alkylation reactions. The designed ligand facilitated the formation of various gamma-vinyl ketones with good regio- and enantio-selectivity using an in situ formed Cu/Zn hetero-bimetallic complex. Computational studies supported the role of ligand-substrate steric interactions in determining the stereoselective outcome.
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 gamma-vinyl ketones with good regio- and enantio-selectivity. DF sT calculation supports that the chelation of allyl phosphates with catalyst promotes the S(N)2' addition and the ligand-substrate steric interactions account for the stereoselective outcome.
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