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 journalJournal articlepeer-review

70 Citations (Scopus)

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
Number of pages7
JournalACS Catalysis
Volume9
Issue number2
DOIs
Publication statusPublished - 7 Jan 2019

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