Journal
ACS CATALYSIS
Volume 9, Issue 2, Pages 1457-1463Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04787
Keywords
asymmetric catalysis; hydrophosphination; chiral phosphine; alkene; ligand design
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Funding
- Shenzhen Basic Research Program [JCYJ20170817112532779, JCYJ20170412152435366]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17213101]
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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.
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