The absolute configuration at the chiral sulfurs centers of (−)-(S S , 1R, 2S, 5R)-menthyl-p-tolylsulfinate (1) and (S S )-[(p-tolyl)sulfinyl]ferrocene (2) were determined by single crystal X-ray diffraction with anomalous dispersion effects and the corresponding calculation of Flack’s absolute structure parameters. Both compounds crystallize in the monoclinic crystal system in space group P21 (no. 4); chiral sulfinate ester 1: a = 8.2868(6), b = 6.1399(3), c = 16.366(2) Å, β = 91.816(6)°, V = 832.3(2) Å3, Z = 2 and absolute structure parameter −0.03(7); chiral ferrocenyl sulfoxide 2: a = 5.8371(3), b = 15.390(2), c = 16.143(2) Å, β = 97.748(6)°, V = 1436.9(3) Å3, Z = 4 and absolute structure parameter +0.01(1). The trigonal pyramidal geometry at the chiral sulfur atom of 2 is close to expected values while the one of 1 is slightly distorted. With direct determination of the absolute configuration at the chiral sulfur centers an important gap concerning the widely used precursors 1 and 2 for the syntheses of chiral sulfoxides and 1,2-disubstituted planar chiral ferrocenyl ligands is now closed. The latter substance class is playing a key role in enantioselective catalysis.
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Financial support by the Deutsche Forschungsgemeinschaft (SFB 583) and the Kunststoff- und Metallwarenfabrik Erlangen (KUM) GmbH & Co. KG is gratefully acknowledged.
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CCDC-602308 for sulfinate 1 and CCDC-602309 for Kagan’s template 2 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK (fax: ++44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
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Heinemann, F.W., Weber, I. & Zenneck, U. Crystal structures of (−)-(S S , 1R, 2S, 5R)-menthyl p-tolyl sulfinate and (+)-(S S )-[(p-tolyl)sulfinyl]ferrocene. J Chem Crystallogr 37, 165–170 (2007). https://doi.org/10.1007/s10870-006-9177-2
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DOI: https://doi.org/10.1007/s10870-006-9177-2