Enantioselective Palladium‐Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides

• Published in: Angewandte Chemie International Edition Vol. 60; no. 52; pp. 27288 - 27292
• Main Authors: Yang, Zhiping, Wang, Jun (Joelle)
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 20-12-2021
• Edition: International ed. in English
• Subjects: allene; allylic compound; Cholesterol; Construction; Enantiomers; Functional groups; hydrophosphinylation; Oxides; Palladium; Phosphine; Phosphine oxide; synthetic method; allene; palladium; allylic compound; synthetic method; hydrophosphinylation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202112285

A Pd‐catalyzed hydrophosphinylation of alkyl and aryl‐oxyallenes with phosphine oxides has been developed for the efficient and rapid construction of a family of chiral allylic phosphine oxides with a diverse range of functional groups. This methodology was further applied in the facile construction of chiral 2H‐chromene and later stage functionalization of cholesterol.
A highly efficient, versatile and atom‐economic protocol to chiral allylic phosphine oxides is demonstrated via palladium‐catalyzed asymmetric hydrophosphinylation of allenes with phosphine oxides. A family of chiral allylic phosphine oxides with a diverse range of functional groups were obtained in high yield (up to 99 %) and enantioselectivities (up to 99 % ee).