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Title: 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
Authors: Kothandaraman, Prasath
Koh, Bing Qin
Limpanuparb, Taweetham
Hirao, Hajime
Chan, Philip Wai Hong
Issue Date: 2013
Source: Kothandaraman, P., Koh, B. Q., Limpanuparb, T., Hirao, H.,& Chan, P. W. H. (2013). 1-(2′-Anilinyl)prop-2-yn-1-ol Rearrangement for Oxindole Synthesis. Chemistry - A European Journal, 19(6), 1978-1985.
Series/Report no.: Chemistry - a European journal
Abstract: A synthetic method that relies on NIS (N-iodosuccinimide)-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 has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving 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. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity.
ISSN: 0947-6539
DOI: 10.1002/chem.201202606
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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