AI Article Synopsis
- Two epoxidation catalysts featuring VANOL ligands—one with aluminum and the other with boron—are compared for their efficiency in catalytic asymmetric epoxidation.
- Both catalysts yield high efficiencies and excellent asymmetric inductions when applied to various aldehydes.
- The aluminum catalyst operates effectively at 0 °C while the boron catalyst functions at -40 °C, producing opposite enantiomers despite high enantioselectivity (up to 99% ee).
Article Abstract
Two epoxidation catalysts, one of which consists of two VANOL ligands and an aluminum and the other that consists of two VANOL ligands and a boron, were compared. Both catalysts are highly effective in the catalytic asymmetric epoxidation of a variety of aromatic and aliphatic aldehydes with diazoacetamides, giving high yields and excellent asymmetric inductions. The aluminum catalyst is effective at 0 °C and the boron catalyst at -40 °C. Although both the aluminum and boron catalysts of ()-VANOL give very high asymmetric inductions (up to 99% ee), they give opposite enantiomers of the epoxide. The mechanism, rate- and enantioselectivity-determining step, and origin of enantiodivergence are evaluated using density functional theory calculations.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10956421 | PMC |
| http://dx.doi.org/10.1021/acscatal.3c03929 | DOI Listing |
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