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Org Lett. 2019 Feb 1;21(3):807-811. doi: 10.1021/acs.orglett.8b04084. Epub 2019 Jan 16.

Extending the Substrate Scope in the Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with Ir-P Stereogenic Aminophosphine-Oxazoline Catalysts.

Author information

1
Departament de Química Física i Inorgànica , Universitat Rovira i Virgili , C/Marcel·lí Domingo, 1 , 43007 Tarragona , Spain.
2
Institute for Research in Biomedicine (IRB Barcelona) , The Barcelona Institute of Science and Technology (BIST) , C/Baldiri Reixac, 10 , 08028 Barcelona , Spain.
3
Departament Química Inorgànica i Orgànica, Secció Orgànica , Universitat de Barcelona , C/Martí i Franquès, 1 , 08028 Barcelona , Spain.

Abstract

Air-stable and readily available Ir-catalyst precursors modified with MaxPHOX-type ligands have been successfully applied in the challenging asymmetric hydrogenation of tetrasubstituted olefins under mild reaction conditions. Gratifyingly, these catalyst precursors are able to efficiently hydrogenate not only a range of indene derivatives (ee's up to 96%) but also 1,2-dihydronapthalene derivatives and acyclic olefins (ee's up to 99%), which both constitute the most challenging substrates for this transformation.

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