Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
Bram B. C. Peters, Jira Jongcharoenkamol, Suppachai Krajangsri, Pher G. Andersson
Abstract
Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.
Topics & Concepts
StereocenterEnantioselective synthesisIridiumConjugated systemChemistryAsymmetric hydrogenationCatalysisEnantiomerCombinatorial chemistryDenticityOptically activeNoyori asymmetric hydrogenationOrganic chemistryCrystal structurePolymerAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry