Abstract
(3S )-4-Methoxybutane-1,3-diol [(S )-4 ], an important auxiliary for the synthesis of planar-chiral metallocenes, has been obtained from (S )-1,2,4-butanetriol via formation of an isomerically pure acetal of p -nitrobenzaldehyde, O-methylation and hydrolysis. Diol (S )-4 was used in a synthesis of the new planar-chiral ferrocene (pS )-1-(diphenylphosphino)-2-formyl-1′,2′,3′,4′,5′-pentamethylferrocene [(pS )-9 ].
Key words
acetals - asymmetric synthesis - chiral pool - lithiation - metallocenes
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9 Crystal Data for (pS )-9 : C28 H29 FeOP, MW = 468.33, monoclinic, space group P 21 /c , a = 9 3345 (1) Å, b = 14 1901 (2) Å, c = 27 7268 (3) Å, β = 98 691 (1)°, V = 3630.45 (8) Å3 , Z = 6, Dcalcd = 1.285 g/cm3 , crystal size 0.28 × 0.26 × 0.26 mm3 . Intensity data were collected at 200(2) K with Mo-Kα radiation (λ = 0.71073 Å). A total of 16501 independent reflections were measured in range 0.74 < Θ < 26.00° and 14474 reflections were considered as observed applying the condition I > 2σ(I). The crystal used for X-ray diffraction was grown in a solution of CH2 Cl2 and pentane. All calculations were performed using the SHELXL-97 program. Structure solved by direct methods and refined against F2 with a Full-matrix least-squares algorithm. Hydrogen atoms were treated using appropriate riding models. Flack absolute structure parameter 0.002 (9), goodness of fit 1.02 for observed reflections, final residual values R 1 (F) = 0.040, wR 2 (F2 ) = 0.096 for observed reflections, residual electron density -0.47 to 1.13 e Å- 3. CCDC 296455 contains the supplementary crystallographic data for this structure. The data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK; fax: +44 1223 336033; email: deposit@ccdc.cam.ac.uk).
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