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The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita-Baylis-Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).
β-Trifluoromethyl (CF3 ) enones were proved to act as good dienophiles in asymmetric normal-electron-demand Diels-Alder cycloadditions with 2,4-dienals under trienamine catalysis with a chiral secondary amine. The sequential reductive amination transformations with benzylamine produced cis- and trans-fused chiral trifluoromethylated octahydroisoquinolines… (More)
An asymmetric exo-Diels-Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo-… (More)