Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis

Zhiwu Lu, Haoyang Zhang, Zhiping Yang, Ning Ding, Ling Meng, Jun Wang*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C═C double bond, but substrates involving nonpolar C═C bonds remain difficult and are rarely tackled. Herein, we report asymmetric hydrophosphination of a non-electronically activated double bond with a remarkably high degree of stereocontrol. This strategy offered an expedient and broadly applicable platform to prepare tertiary phosphines in high yields (up to 99% yield) and enantioselectivities (up to 99% ee). Particularly noteworthy is that these tertiary phosphine products were then successfully employed as phosphine ligands in enantioselective metal-catalyzed transformations with a high level of asymmetric induction.

Original languageEnglish
Pages (from-to)1457–1463
JournalACS Catalysis
Volume9
Issue number2
DOIs
Publication statusPublished - 7 Jan 2019

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