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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801703
Subject(s) - enantioselective synthesis , rhodium , chemistry , catalysis , steric effects , diastereomer , enantiomer , stereoselectivity , ligand (biochemistry) , cyclopentadienyl complex , chiral ligand , stereochemistry , combinatorial chemistry , organic 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 ).