A metal-free oxidative dearomatization of indoles with aromatic ketones mediated by TEMPO oxoammonium salt is described. The dearomatization proceeds smoothly and displays a broad substrate scope with respect to both indoles and aromatic ketones in the presence of H2SO4, affording the corresponding 2,2-disubstituted indolin-3-ones in good yields.
Reported here is an efficient enantioselective hydrogenation of cyclic oxocarbenium ions generated in situ through collapse of corresponding acetal substrates. The asymmetric approach provides a straightforward access to a variety of chiral α-aryl substituted 1,3-dihydroisobenzofurans in high yields with excellent enantioselectivities.α-Alkynyl substituted 1,3-dihydroisobenzofurans were also proved to be suitable substrates. In addition, when the reaction was performed at gram scale, the desired product was obtained in good yields with excellent enantioselectivity.
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