AI Article Synopsis
- - A new method using palladium as a catalyst has been developed to create complex seven-membered cyclic structures from spirovinylcyclopropanyl oxindoles and cyclic -sulfonylimines.
- - This process produces a variety of benzosultams with high yields (average 87%) and good selectivity in terms of how the molecules are arranged spatially (diastereoselectivities).
- - The technique also allows for the creation of enantioenriched (optically active) benzosultams efficiently, showcasing its practical application in larger-scale reactions and further chemical transformations.
Article Abstract
A palladium-catalyzed ring-opening [3 + 2]-annulation of spirovinylcyclopropanyl oxindoles with seven-membered cyclic -sulfonylimines has been developed. A wide range of seven-membered benzosultams featuring both a quaternary center and axially chiral biaryl scaffolds have been afforded in an average yield of 87% with moderate to excellent diastereoselectivities. The enantioenriched benzosultams were also accessed successfully in good yields with excellent atropoenantioselectivities enabled by the Pd(dba)/(,,)-SKP ligand. The practical utility of this protocol was further demonstrated by the gram-scale reaction and diversified synthetic transformations of the desired seven-membered benzosultam.
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| http://dx.doi.org/10.1021/acs.orglett.3c01422 | DOI Listing |
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