AI Article Synopsis
- A chiral '-dioxide/Mg(II) complex Lewis acid catalyst enabled a highly selective cascade reaction of Morita-Baylis-Hillman maleimides with -hydroxychalcones, leading to the formation of spiro[cyclopentane-1,3'-oxindole] compounds.
- The method shows excellent efficiency with up to 99% yield and good compatibility with various functional groups, producing compounds that feature five consecutive stereocenters.
- Additionally, the study observed ligand acceleration and chiral amplification effects, and demonstrated potential applications with gram-scale synthesis and positive effects on A549 cell viability.
Article Abstract
A highly diastereo- and enantioselective cascade annulation reaction of Morita-Baylis-Hillman (MBH) maleimides of isatins with -hydroxychalcones was achieved by a chiral '-dioxide/Mg(II) complex Lewis acid catalyst. This strategy provides a concise and efficient route to densely functionalized spiro[cyclopentane-1,3'-oxindole] compounds with five consecutive stereocenters. The reaction itself features mild conditions, good functional group compatibility, and broad substrate scope (62 examples, up to 99% yield, up to >20:1 dr, 97% ee). In addition, an obvious ligand acceleration effect and chiral amplification effect were observed. DFT calculations were performed to elucidate the stereoselectivity observed. The gram-scale synthesis and the inhibitory effect of two products on the viability of A549 cells demonstrate the potential utility of the current method.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.4c02173 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!