Enantioselective Intramolecular Hydroarylation of Alkenes via Directed C-H Bond Activation

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Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe){sub 2}]{sub 2} and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% ee for each substrate class. Cyclization of substrates with Z-alkene isomers proceeded much more efficiently than substrates with E-alkene isomers. This further enabled the highly stereoselective intramolecular alkylation of certain substrates containing Z/E-alkene mixtures via a Rh-catalyzed alkene isomerization with preferential cyclization of the Z-isomer.

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Harada, Hitoshi; Thalji, Reema; Bergman, Robert & Ellman, Jonathan May 22, 2008.

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Highly enantioselective catalytic intramolecular ortho-alkylation of aromatic imines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using [RhCl(coe){sub 2}]{sub 2} and chiral phosphoramidite ligands. Cyclization of substrates containing 1,1- and 1,2-disubstituted as well as trisubstituted alkenes were achieved with enantioselectivities >90% ee for each substrate class. Cyclization of substrates with Z-alkene isomers proceeded much more efficiently than substrates with E-alkene isomers. This further enabled the highly stereoselective intramolecular alkylation of certain substrates containing Z/E-alkene mixtures via a Rh-catalyzed alkene isomerization with preferential cyclization of the Z-isomer.

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  • Journal Name: Journal of Organic Chemistry

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  • Report No.: LBNL-1511E
  • Grant Number: DE-AC02-05CH11231
  • DOI: 10.1021/jo801098z | External Link
  • Office of Scientific & Technical Information Report Number: 948473
  • Archival Resource Key: ark:/67531/metadc902286

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  • May 22, 2008

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  • Sept. 27, 2016, 1:39 a.m.

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  • Sept. 30, 2016, 6:27 p.m.

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Harada, Hitoshi; Thalji, Reema; Bergman, Robert & Ellman, Jonathan. Enantioselective Intramolecular Hydroarylation of Alkenes via Directed C-H Bond Activation, article, May 22, 2008; Berkeley, California. (digital.library.unt.edu/ark:/67531/metadc902286/: accessed September 26, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.