Stereoselective Synthesis of trans-β-Substituted γ-Ferrocenyl-γ-butyrolactones via Ammonium Ylides

Abstract

trans-b-substituted γ-ferrocenyl-γ-butyrolactones were prepared via the reaction of quaternary ammonium salts with electron-deficient trisubstituted alkene 1 under the optimum conditions. Moderate to good yields and excellent trans stereoselectivity were achieved for the new compounds 2-10. The X-ray crystal structure of 2a was determined and all the products were characterized by ¹H NMR, ¹³C NMR, FAB-MS, IR and HRMS spectra.

Key words

trans-β-substituted γ-ferrocenyl-γ-butyrolactones - ammonium ylides - electron-deficient - stereoselectivity - mechanism

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10

Crystal Data for 2a: C₂₁H₁₈FeO₃, MW = 374.20, monoclinic, space group P2(1)/c, a = 21.048(3)Å, b = 7.480(1)Å, c = 11.020(1)Å, α = 90.00°, β = 90.45(1)°, γ = 90.00°, V = 1716.19(38)ų, Z = 4, Dc = 1.448 mg/m³, F(000) = 776, crystal size 0.58 × 0.56 × 0.36mm, Intensity data were collected at 291 (2) K with a Siemens P4 diffractometer with graphite monochromator, and MoKα radiation (λ = 0.71073 Å,). A total of 3371 independent reflections were measured in range 1.96 < θ < 26.00° and 2293 reflections were considered as observed applying the condition I >2σ(I). The crystal used for X-ray diffraction was grown in a solution of acetone and petroleum ether. All calculations were performed using the SHELXL-97 program. The non-hydrogen atoms were refined anisotropically and the hydrogen atoms were included but not refined. The final cycle of full matrix least-square refinement was based on F². The final R and Rw values were 0.0328 and 0.0765 respectively. Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Center, CCDC No. 266936 for compound 2a. Copies of this information may be obtained free of charge from: The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK, Fax (int. code):
[phone]; email:[e-mail] or
http://www.ccdc.cam.ac.uk.