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Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation.
- Source :
-
Tetrahedron . Jun2020, Vol. 76 Issue 25, pN.PAG-N.PAG. 1p. - Publication Year :
- 2020
-
Abstract
- A series of enantioenriched ferrocenyl monophosphines imbued with both central and planar chirality were obtained catalytically (80–99% ee) via the kinetic resolution of 1,2-disubstituted planar chiral ferrocenyl enone racemates. The synthetic approach utilized a chiral palladacycle to facilitate the asymmetric hydrophosphination (AHP) as a means to achieve high stereoselectivity. The enantioenriched ferrocenylphosphine products could be protected and further recrystallized to obtain ee s up to 99%. The modularity of the phosphine framework obtained was demonstrated via derivatization of its functional handles via a simple nucleophilic substitution to yield optically pure bisphosphines. Image 1 • Route towards ferrocenyl phosphines bearing both central and planar stereogenic elements. • Employs catalytic asymmetric P–H addition protocol to achieve efficient kinetic resolution. • Allows generation of 1,2 diphosphines from racemic substrates. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 76
- Issue :
- 25
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 143551433
- Full Text :
- https://doi.org/10.1016/j.tet.2020.131259