Efficient synthesis of optically active Nfused 1,3-oxazolidines containing quaternary and tertiary stereocenters was achieved via Pd-catalyzed asymmetric (3 + 2) cycloadditions of sulfamatederived cyclic imines and vinylethylene carbonates. Using a chiral phosphoramidite ligand, the cycloadditions proceeded effectively providing sulfamidate-fused 1,3-oxazolidines in high yields (up to 96%) with stereoselectivities (up to 25:1 dr; > 99% ee). Additionally, the scale-up reaction and further transformations of the product were also achieved demonstrating the synthetic utility toward the construction of useful heterocycles such as chiral oxazoline bearing a quaternary stereocenter.Scheme 2. Gram-scale synthesis of sulfamidate-fused 1,3-oxazolidine 3 a and its further applications.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.