The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)-catalyzed allylic C–H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C–H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported to date (avg. 92% ee, 13 examples with great than 90% ee).

Enantioselective allylic C–H oxidation of terminal olefins to isochromans by palladium(II)/chiral sulfoxide catalysis

253rd National Meeting (2017)

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