AI Article Synopsis
- A new type of highly activated donor-acceptor cyclopropanes with a single vinylogous acceptor has been developed, which can undergo reactions with various substrates like aldehydes and ketones to form different cyclic compounds.
- Researchers found that the choice of catalyst determines the diastereoselectivity in these reactions, allowing for control over the product's configuration.
- The study involved detailed mechanistic and kinetic experiments to understand the catalytic cycle and the reasons behind the specific stereochemical results observed.
Article Abstract
A novel class of highly activated donor-acceptor cyclopropanes bearing only a single, vinylogous acceptor is presented. These strained moieties readily undergo cycloadditions with aldehydes, ketones, thioketones, nitriles, naphth-2-ols and various other substrates to yield the corresponding carbo- and heterocycles. Diastereocontrol can be achieved through the choice of catalyst (Brønsted or Lewis acid). The formation of tetrahydrofurans was shown to be highly enantiospecific when chiral cyclopropanes are employed. A series of mechanistic and kinetic experiments was conducted to elucidate a plausible catalytic cycle and to rationalize the stereochemical outcome.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10099577 | PMC |
| http://dx.doi.org/10.1002/anie.202214390 | DOI Listing |
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