Catalytic access to ferrocenyl phosphines bearing both planar and central chirality – A kinetic resolution approach via catalytic asymmetric P(III)–C bond formation

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 th...

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Veröffentlicht in:Tetrahedron 2020-06, Vol.76 (25), p.131259, Article 131259
Hauptverfasser: Sadeer, Abdul, Kojima, Tadayuki, Ng, Jia Sheng, Gan, Kennard, Chew, Renta Jonathan, Li, Yongxin, Pullarkat, Sumod A.
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Sprache:eng
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Zusammenfassung: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 ees 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. [Display omitted] •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.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131259