Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates | Zendy

Wenyong Chen | Zendy; Ming Chen | Zendy; John F. Hartwig | Zendy

Open Access

Diastereo- and Enantioselective Iridium-Catalyzed Allylation of Cyclic Ketone Enolates: Synergetic Effect of Ligands and Barium Enolates

Author(s) -

Wenyong Chen,

Ming Chen,

John F. Hartwig

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja506500u

Subject(s) - chemistry , enantioselective synthesis , stereocenter , iridium , phosphoramidite , ketone , allylic rearrangement , ethylamine , ligand (biochemistry) , catalysis , alkylation , tsuji–trost reaction , chiral ligand , medicinal chemistry , organic chemistry , dna , biochemistry , receptor , oligonucleotide

We report asymmetric allylic alkylation of barium enolates of cyclic ketones catalyzed by a metallacyclic iridium complex containing a phosphoramidite ligand derived from (R)-1-(2-naphthyl)ethylamine. The reaction products contain adjacent quaternary and tertiary stereocenters. This process demonstrates that unstabilized cyclic ketone enolates can undergo diastereo- and enantioselective Ir-catalyzed allylic substitution reactions with the proper choice of enolate countercation. The products of these reactions can be conveniently transformed to various useful polycarbocyclic structures.

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