Asymmetric Synthesis of N-Fused 1,3-Oxazolidines via Pd-Catalyzed Decarboxylative (3+2) Cycloaddition
- Park, Jong-Un; Ahn, Hye-In; Cho, Ho-Jun; Xuan, Zi; Kim, Ju Hyun
- Issue Date
- WILEY-V C H VERLAG GMBH
- Oxazolidines; Cycloaddition; Asymmetric catalysis; Sulfamidates; Quaternary stereocenter
- ADVANCED SYNTHESIS & CATALYSIS, v.362, no.9, pp.1836 - 1840
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Start Page
- End Page
- Efficient synthesis of optically active N-fused 1,3-oxazolidines containing quaternary and tertiary stereocenters was achieved via Pd-catalyzed asymmetric (3+2) cycloadditions of sulfamate-derived 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.
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