Chemoselective and Enantioselective Hydrogenation of 2, 4‐Diaryl‐3H‐benzo[b]azepines Catalyzed by Dendritic Phosphinooxazoline Iridium Complexes. Issue 9 (13th April 2017)

• Record Type: Journal Article
• Authors: Miao, Tingting; Ma, Baode; Ding, Ziyuan; Liu, Youran; He, Yan‐Mei; Fan, Qing‐Hua
• Is Part Of: Asian journal of organic chemistry. Volume 6:Issue 9(2017)
• Page Start: 1219
• Page End: 1221
• Publication Date: 2017-04-13
• Subjects: asymmetric catalysis -- benzo[b]azepine -- dendrimers -- hydrogenation -- N, P ligands; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201700094
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An asymmetric hydrogenation of 2, 4‐diaryl‐3 H ‐benzo[ b ]azepines, catalyzed by dendritic phosphinooxazoline (PHOX) iridium complexes, has been developed. Only the imine group was reduced, while the C=C bond remained untouched, affording a range of chiral 2, 3‐dihydro‐1 H ‐benzo[ b ]azepine derivatives with good to excellent enantioselectivity (up to 91 % ee ). A slightly positive dendritic effect on catalytic reactivity (up to 10 000 TON) was observed. Abstract : Imine vs. olefin : The title reaction was achieved in the presence of chiral dendritic phosphinooxazoline (PHOX) iridium complexes, affording enantioenriched 2, 3‐dihydro‐1 H ‐benzo[ b ]azepine derivatives with good to excellent enantioselectivity.