American Chemical Society
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Stereoselective Oxindole Synthesis by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Amides

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journal contribution
posted on 2009-05-21, 00:00 authored by Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami
A new cyclization reaction occurred on treatment of 2-(alkynyl)aryl isocyanates with amides in the presence of a palladium(0)/diphosphine catalyst to stereoselectively form 3-(amidoalkylidene)oxindoles. A carbon−nitrogen bond as well as a carbon−carbon bond were simultaneously introduced onto the alkyne moiety to construct an oxindole skeleton with stereoselective placement of the amino substituent cis to the carbonyl group.