A Planar‐Chiral Rhodium(III) Catalyst with a Sterically Demanding Cyclopentadienyl Ligand and Its Application in the Enantioselective Synthesis of Dihydroisoquinolones | Zendy

Trifonova Evgeniya A. | Zendy; Ankudinov Nikita M. | Zendy; Mikhaylov Andrey A. | Zendy; Chusov Denis A. | Zendy; Nelyubina Yulia V. | Zendy; Perekalin Dmitry S. | Zendy

Premium

A Planar‐Chiral Rhodium(III) Catalyst with a Sterically Demanding Cyclopentadienyl Ligand and Its Application in the Enantioselective Synthesis of Dihydroisoquinolones

Author(s) -

Trifonova Evgeniya A.,

Ankudinov Nikita M.,

Mikhaylov Andrey A.,

Chusov Denis A.,

Nelyubina Yulia V.,

Perekalin Dmitry S.

Publication year - 2018

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.201801703

Subject(s) - enantioselective synthesis , rhodium , chemistry , catalysis , steric effects , diastereomer , stereoselectivity , enantiomer , cyclopentadienyl complex , ligand (biochemistry) , planar chirality , stereochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , biochemistry , receptor

The rapid development of enantioselective C−H activation reactions has created a demand for new types of catalysts. Herein, we report the synthesis of a novel planar‐chiral rhodium catalyst [(C 5 H 2 t Bu 2 CH 2 t Bu)RhI 2 ] 2 in two steps from commercially available [(cod)RhCl] 2 and tert ‐butylacetylene. Pure enantiomers of the catalyst were obtained through separation of its diastereomeric adducts with natural ( S )‐proline. The catalyst promoted enantioselective reactions of aryl hydroxamic acids with strained alkenes to give dihydroisoquinolones in high yields (up to 97 %) and with good stereoselectivity (up to 95 % ee ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research