An efficient method is developed for preparing functionalized axially chiral compounds via the ring-opening reaction of cyclic diaryliodonium salts. Two conformers of the cyclic diaryliodonium salt observed in the crystal structure underwent quick equilibration. The distortion of the diaryliodonium salts significantly increased reactivity toward the chiral copper catalyst, which enabled the reaction to take place in mild conditions to furnish the products in enantioselectivities up to 99.5:0.5 (R:S).
A Cu‐catalyzed asymmetric ring‐opening reaction between cyclic diaryliodonium and benzylic or aliphatic amines has been developed. At low concentration of the amines, realized by either mixing the amines with Lewis acid or slow addition of the amines, the reaction afforded the products in high enantioselectivity.magnified image
A catalytically asymmetric palladium/norbornene-catalyzed reaction is reported, where α-aryl tetrahydroquinoline derived phosphoramidite L15 is found to be the optimum ligand. Taking advantage of this transformation, the concise and unified enantioselective syntheses of (+)-rhazinal, (+)-rhazinilam, and (+)-kopsiyunnanine C1, C2, and C3 are realized.
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