The formal [3+2] cycloaddition of epoxides and unsaturated compounds is a powerful methodology for the synthesis of densely functionalized five-membered heterocyclic compounds containing oxygen. Described is a novel enantioselective formal [3+2] cycloaddition of epoxides under Brønsted base catalysis. The bis(guanidino)iminophosphorane as a chiral organosuperbase catalyst enabled the enantioselective reaction of β,γ-epoxysulfones with imines, owing to its strong basicity and high stereocontrolling ability, to provide enantioenriched 1,3-oxazolidines having two stereogenic centers, including a quaternary one, in a highly diastereo- and enantioselective manner.
The formal [3+ +2] cycloaddition of epoxides and unsaturated compounds is ap owerfulm ethodology for the synthesis of densely functionalizedfive-membered heterocyclic compounds containing oxygen. Described is an ovel enantioselective formal [3+ +2] cycloaddition of epoxides under Brønsted base catalysis.The bis(guanidino)iminophosphorane as ac hiral organosuperbase catalyst enabled the enantioselective reaction of b,g-epoxysulfones with imines,o wingt oi ts strong basicity and high stereocontrolling ability,t op rovide enantioenriched 1,3-oxazolidines having two stereogenic centers,i ncluding aq uaternary one,i nah ighly diastereo-and enantioselective manner. Scheme 1. Designedr eaction system.P G= protecting group.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.
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