4.0 Article

Synthesis and characterization of enantiopure planar-chiral phosphorus-linked diferrocenes

Journal

Publisher

INT UNION CRYSTALLOGRAPHY
DOI: 10.1107/S2053229621001996

Keywords

crystal structure; metal organic; three-dimensional structure; ferrocene; phosphine; sulfide; chirality; planar chirality

Funding

  1. Projekt DEAL

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In the course of a synthetic project on cyclic diferrocenylphosphines, planar-chiral diferrocenyl compounds were obtained as precursors for subsequent cyclization. The crystal structures of two symmetric compounds were reported, one containing four stereogenic centers and the other being a purely planar-chiral compound. Reactions performed on these compounds strongly favored one ferrocene unit over the other due to diastereoselectivity, demonstrating the impact of stereochemistry on reactivity.
In the course of an ongoing synthetic project on cyclic diferrocenylphosphines, we obtained a group of planar-chiral diferrocenyl compounds useful as precursors for subsequent cyclization. Here we report the crystal structures of two symmetric compounds [(FcA)2(Ph)P], one of which contains four stereogenic centres (two C chiral and two planar chiral centres), i.e. 1,10-(phenylphosphanediyl)bis{(2Sp)-2-[(1R)-1-(acetyloxy)ethyl]ferrocene}, [Fe2(C5H5)2(C24H25O4P)], and the other phosphine sulfide is a purely planar-chiral compound (two planar chiral centres), i.e. bis[(2Sp)-2-ethenylferrocen-1-yl]phenylphosphane sulfide, [Fe2(C5H5)2(C20H17PS)]. Owing to the stereocentres present, reactions performed on [(FcA)2(Ph)P]-type compounds strongly favour one ferrocene unit over the other due to diastereoselectivity. Furthermore, we present four related structures where the ferrocene units are not identical [(FcA)(Fc B)(Ph)P]. These are {(2Sp)-2-[(1R)-1-(acetyloxy)ethyl]ferrocen-1-yl}[(2Sp)-2-ethenylferrocen-1yl]phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C22H21O2PS)], [(2Sp)-2-ethenylferrocen-1-yl]{(2Sp)-2-[(1R)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C20H19OPS)], {(2Sp)-2-[(1R)-1-(acetyloxy)ethyl]ferrocen-1yl}{(2Sp)-2-[(1R)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(R)-phosphine sulfide, [Fe2(C5H5)2(C22H23O3PS)], and {(2Sp)-2-[(1R)-1-benzylamino)ethyl] ferrocen1-yl}[(2Sp)-2-ethenylferrocen-1-yl]phenyl-(S)-phosphine sulfide, [Fe2(C5H5)2(C27H26NPS)]. All of the structures are accessible in one step from known precursors.

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