Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

• Published in: Chemical communications (Cambridge, England) Vol. 58; no. 2; pp. 262 - 265
• Main Authors: Song, Jingyuan, Shao, Pan-Lin, Wang, Jiang, Huang, Fanping, Zhang, Xumu
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 23.12.2021; Royal Society of Chemistry
• Subjects: Asymmetry; Chemistry; Chemistry, Multidisciplinary; Coordination compounds; Diketones; Diols; Hydrogenation; Iridium compounds; Physical Sciences; Science & Technology; KETONES; HIGHLY ENANTIOSELECTIVE HYDROGENATION; EFFICIENT APPROACH; LIGANDS; ALKYL TERMINAL AZIRIDINES; STEREOSELECTIVE HYDROGENATION; C2-SYMMETRICAL BIS(PHOSPHOLANES); IRIDIUM CATALYSTS; ACCESS; CYCLIC AMINES
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d1cc05359k

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herein report an efficient asymmetric hydrogenation of 1,4-diaryldiketones catalyzed by a chiral iridium complex bearing f -amphox as ligand, furnishing a series of 1,4-diarylbutane-1,4-diols in excellent yields (up to >99%) with exceptional enantioselectivities (up to >99.9% ee) and diastereoselectivities (up to >100 : 1 dr). Presented herein is anIr/ f -amphox-catalyzed asymmetric hydrogenation for accessing enantiopure 1,4-diarylbutane-1,4-diolsin superb yields with exceptional stereoselectivities.