Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium-Catalyzed C----C Bond-Forming Transfer Hydrogenation

Oxindoles with a twist: Transfer hydrogenation of substituted isatins in the presence of allyl acetate, α‐methyl allyl acetate, or 1,1,‐dimethylallene using an cyclometalated iridium catalyst, provides products of carbonyl allylation, crotylation, and reverse prenylation, respectively, in highly ena...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2009-08, Vol.48 (34), p.6313-6316
Hauptverfasser:	Itoh, Junji, Han, Soo Bong, Krische, Michael J
Format:	Artikel
Sprache:	eng
Schlagworte:	allylation Catalysis crotylation enantioselectivity Hydrogenation iridium Iridium - chemistry Isatin - chemistry Prenylation Stereoisomerism transfer hydrogenation
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creator	Itoh, Junji Han, Soo Bong Krische, Michael J
description	Oxindoles with a twist: Transfer hydrogenation of substituted isatins in the presence of allyl acetate, α‐methyl allyl acetate, or 1,1,‐dimethylallene using an cyclometalated iridium catalyst, provides products of carbonyl allylation, crotylation, and reverse prenylation, respectively, in highly enantiomerically enriched form. These studies represent the first use of activated ketones as electrophilic partners in asymmetric CC bond‐forming transfer hydrogenation.
doi_str_mv	10.1002/anie.200902328
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subjects	allylation Catalysis crotylation enantioselectivity Hydrogenation iridium Iridium - chemistry Isatin - chemistry Prenylation Stereoisomerism transfer hydrogenation
title	Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium-Catalyzed C----C Bond-Forming Transfer Hydrogenation
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