AI Article Synopsis
- A method for creating polysubstituted spirocyclopropyl oxindoles using rare-earth metal salts, specifically Sc(OTf), has been developed.
- This technique involves a multicomponent reaction that showcases high diastereoselectivity, achieving ratios of up to 94:6 for the different isomers.
- Computational studies suggest that the unique properties of the metal, such as its ability to coordinate and its preference for oxygen, are crucial in producing the predominant isomer in the reaction.
Article Abstract
The synthesis of polysubstituted spirocyclopropyl oxindoles using a series of rare-earth metal (REM) salts is reported. REMs, in particular Sc(OTf), allowed access to the target compounds by a multicomponent reaction with high diastereoselectivity (≤94:6:0:0). Density functional theory calculations on the model reaction are consistent with the observed selectivity and revealed that the special coordinating capabilities and the oxophilicity of the metal are key factors in inducing the formation of one main diastereoisomer.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167684 | PMC |
| http://dx.doi.org/10.1021/acs.orglett.3c00772 | DOI Listing |
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