Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins. (21st January 2020)

• Record Type: Journal Article
• Authors: Bigler, Raphael; Mack, Kyle A.; Shen, Jeff; Tosatti, Paolo; Han, Chong; Bachmann, Stephan; Zhang, Haiming; Scalone, Michelangelo; Pfaltz, Andreas; Denmark, Scott E.; Hildbrand, Stefan; Gosselin, Francis
• Is Part Of: Angewandte Chemie. Volume 132:Number 7(2020)
• Page Start: 2866
• Page End: 2871
• Publication Date: 2020-01-21
• Subjects: Asymmetrische Katalyse -- Hydrierungen -- Iridium -- N, P-Liganden -- Tetrasubstituierte Olefine; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201912640
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio‐ and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio‐ and diastereoselectivity. Abstract : Die Optimierung des Liganden im Iridiumkatalysator ermöglicht die asymmetrische Hydrierung nichtfunktionalisierter, tetrasubstituierter, acyclischer Olefine, die zwei vicinale Stereozentren mit exzellenten Stereoselektivitäten einführt.