Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: iridium-catalyzed C-C bond-forming transfer hydrogenation.

Angew Chem Int Ed Engl

University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station-A5300, Austin, TX 78712-1167, USA.

Published: October 2009

AI Article Synopsis

  • The study demonstrates a new method for transferring hydrogen to substituted isatins using a specific iridium catalyst and different allyl compounds.
  • This process results in the formation of enantiomerically enriched products through carbonyl allylation, crotylation, and reverse prenylation.
  • This research is significant as it showcases the first instance of activated ketones being used in asymmetric C-C bond formation via transfer hydrogenation.

Article Abstract

Transfer hydrogenation of substituted isatins in the presence of allyl acetate, α-methyl allyl acetate or 1,1,-dimethylallene employing an -cyclometallated iridium catalyst modified by CTH-()-P-PHOS 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. [Image: see text]

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2846777PMC
http://dx.doi.org/10.1002/anie.200902328DOI Listing

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