{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:21:28Z","timestamp":1740172888813,"version":"3.37.3"},"reference-count":37,"publisher":"International Union of Crystallography (IUCr)","issue":"3","license":[{"start":{"date-parts":[[2021,2,25]],"date-time":"2021-02-25T00:00:00Z","timestamp":1614211200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,2,25]],"date-time":"2021-02-25T00:00:00Z","timestamp":1614211200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2021,2,19]]},"published-print":{"date-parts":[[2021,3,1]]},"abstract":"<jats:p>In the course of an ongoing synthetic project on cyclic diferrocenylphosphines, we obtained a group of planar\u2013chiral diferrocenyl compounds useful as precursors for subsequent cyclization. Here we report the crystal structures of two symmetric compounds [(Fc<jats:sup>A<\/jats:sup>)<jats:sub>2<\/jats:sub>(Ph)P], one of which contains four stereogenic centres (two C chiral and two planar chiral centres),<jats:italic>i.e.<\/jats:italic>1,1\u2032-(phenylphosphanediyl)bis{(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-(acetyloxy)ethyl]ferrocene}, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>24<\/jats:sub>H<jats:sub>25<\/jats:sub>O<jats:sub>4<\/jats:sub>P)], and the other phosphine sulfide is a purely planar\u2013chiral compound (two planar chiral centres),<jats:italic>i.e.<\/jats:italic>bis[(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)--2-ethenylferrocen-1-yl]phenylphosphane sulfide, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>20<\/jats:sub>H<jats:sub>17<\/jats:sub>PS)]. Owing to the stereocentres present, reactions performed on [(Fc<jats:sup>A<\/jats:sup>)<jats:sub>2<\/jats:sub>(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 [(Fc<jats:sup>A<\/jats:sup>)(Fc<jats:sup>B<\/jats:sup>)(Ph)P]. These are {(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-(acetyloxy)ethyl]ferrocen-1-yl}[(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-ethenylferrocen-1-yl]phenyl-(<jats:italic>S<\/jats:italic>)-phosphine sulfide, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>22<\/jats:sub>H<jats:sub>21<\/jats:sub>O<jats:sub>2<\/jats:sub>PS)], [(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-ethenylferrocen-1-yl]{(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(<jats:italic>S<\/jats:italic>)-phosphine sulfide, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>20<\/jats:sub>H<jats:sub>19<\/jats:sub>OPS)], {(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-(acetyloxy)ethyl]ferrocen-1-yl}{(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-hydroxyethyl]ferrocen-1-yl}phenyl-(<jats:italic>R<\/jats:italic>)-phosphine sulfide, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>22<\/jats:sub>H<jats:sub>23<\/jats:sub>O<jats:sub>3<\/jats:sub>PS)], and {(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-[(1<jats:italic>R<\/jats:italic>)-1-benzylamino)ethyl]ferrocen-1-yl}[(2<jats:italic>S<\/jats:italic><jats:sub>p<\/jats:sub>)-2-ethenylferrocen-1-yl]phenyl-(<jats:italic>S<\/jats:italic>)-phosphine sulfide, [Fe<jats:sub>2<\/jats:sub>(C<jats:sub>5<\/jats:sub>H<jats:sub>5<\/jats:sub>)<jats:sub>2<\/jats:sub>(C<jats:sub>27<\/jats:sub>H<jats:sub>26<\/jats:sub>NPS)]. All of the structures are accessible in one step from known precursors.<\/jats:p>","DOI":"10.1107\/s2053229621001996","type":"journal-article","created":{"date-parts":[[2021,2,25]],"date-time":"2021-02-25T10:29:23Z","timestamp":1614248963000},"page":"152-160","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and characterization of enantiopure planar\u2013chiral phosphorus-linked diferrocenes"],"prefix":"10.1107","volume":"77","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8225-671X","authenticated-orcid":true,"given":"Philipp","family":"Honegger","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander","family":"Roller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Widhalm","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2021,2,25]]},"reference":[{"key":"zo3008_bb1","doi-asserted-by":"crossref","first-page":"4166","DOI":"10.1002\/ejic.200300264","volume":"2003","author":"Barbaro","year":"2003","journal-title":"Eur. 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