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Enantioselective Allylation, Crotylation, and Reverse Prenylation of Substituted Isatins: Iridium‐Catalyzed CC Bond‐Forming Transfer Hydrogenation
Author(s) -
Itoh Junji,
Han Soo Bong,
Krische Michael J.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200902328
Subject(s) - chemistry , library science , stereochemistry , computer science
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 CC bond‐forming transfer hydrogenation.