A straightforward method for synthesizing cyclopenta[]chromanones is demonstrated. The strategy involves a [3+2] cycloaddition of VCPs and activated coumarins under Pd-catalyzed conditions. The reaction provides the desired products bearing up to four consecutive stereocenters with high diastereocontrol. Control experiments and density functional theory studies support the proposed mechanism and the observed diastereoselectivity in the product through a thermodynamically controlled pathway.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c00836 | DOI Listing |
Publication Analysis
Top Keywords
[3+2] cycloaddition
8
diastereoselective synthesis
4
synthesis cyclopenta[]chromanones
4
cyclopenta[]chromanones pd-catalyzed
4
pd-catalyzed [3+2]
4
cycloaddition straightforward
4
straightforward method
4
method synthesizing
4
synthesizing cyclopenta[]chromanones
4
cyclopenta[]chromanones demonstrated
4
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!