A Planar‐Chiral Rhodium(III) Catalyst with a Sterically Demanding Cyclopentadienyl Ligand and Its Application in the Enantioselective Synthesis of Dihydroisoquinolones. (17th April 2018)

• Record Type: Journal Article
• Authors: Trifonova, Evgeniya A.; Ankudinov, Nikita M.; Mikhaylov, Andrey A.; Chusov, Denis A.; Nelyubina, Yulia V.; Perekalin, Dmitry S.
• Is Part Of: Angewandte Chemie. Volume 130:Number 26(2018)
• Page Start: 7840
• Page End: 7844
• Publication Date: 2018-04-17
• Subjects: Asymmetrische Katalyse -- C-H-Aktivierung -- Cyclopentadienyl-Liganden -- Rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201801703
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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 [(C5 H2 t Bu2 CH2 t Bu)RhI2 ]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 ).