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Article Abstract
Ring-opening/cyclization represents a classic reaction of bicyclic diaziridines. In this study, an unprecedented ring-opening/migration cascade process was discovered in the reaction between bicyclic diaziridines and donor-acceptor (D-A) cyclopropanes. By employing a chiral ,'-dioxide/scandium(iii) complex as the catalyst, a diverse array of chiral dihydro-1-pyrazoles with a stereocenter in the side chain was efficiently synthesized featuring excellent ee values. Control experiments indicated that the substitution on the D-A cyclopropane is of critical importance in determining the cyclization or migration process. When combined with DFT calculations, a plausible reaction mechanism was proposed, which involves a key transition state. This work presents a novel method for accessing pyrazolines and broadens the scope of diaziridine chemistry.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12372524 | PMC |
| http://dx.doi.org/10.1039/d5sc04846j | DOI Listing |
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