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

Autor: Trifonova EA; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia., Ankudinov NM; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia., Mikhaylov AA; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia., Chusov DA; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia., Nelyubina YV; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia., Perekalin DS; Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Jun 25; Vol. 57 (26), pp. 7714-7718. Date of Electronic Publication: 2018 Apr 17.
DOI: 10.1002/anie.201801703
Abstrakt: 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).
(© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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