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Dr. Prasath Kothandaraman, Bing Qin Koh, Dr. Taweetham Limpanuparb, Prof. Dr. Hajime Hirao and Prof. Dr. Philip Wai Hong Chan 1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis Chemistry - A European Journal 19

Article first published online: 30 NOV 2012 | DOI: 10.1002/chem.201202606

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Alcohols to oxindoles: A chemoselective synthetic method that relies on NIS-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones was developed (see scheme; NIS=N-iodosuccinimide). Secondary and tertiary alcoholic substrates exclusively gave the 3- and 2-oxindole products, respectively; in the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay.

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