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Efficient asymmetric addition of diethylzinc



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Full Paper Received 24 July 2008 Revised 12 August 2008 Accepted 12 August 2008 Published online in Wiley Interscience 15 September 2008 www interscience com DOI 10 1002 aoc 1457 Efficient asymmetric addition of diethylzinc to aldehydes using 3 hydroxyazetidine derivatives as chiral ligands Ruochen Liu Xuemei Bai Zhanbin Zhang and Guofu Zi A new series of chiral 3 hydroxyazetidines has been prepared from S 1 4 methoxyphenyl ethylamine These ligands have shown excellent catalytic activities and enantiomeric selectivities in asymmetric addition of diethylzinc to aromatic aldehydes c 2008 John Wiley Sons Ltd Copyright Keywords azetidines chiral ligands asymmetric addition diethylzinc aldehyde Introduction Experimental General methods Appl Organometal Chem 2008 22 671 675 All chemicals were purchased from Aldrich Chemical Co and Beijing Chemical Co and used as received unless otherwise noted Infrared spectra were obtained on an Avatar 360 Fourier transform spectrometer 1 H and 13 C NMR spectra were recorded on a Bruker AV 500 spectrometer All chemical shifts were reported in units with reference to the residual protons of the deuterated solvents for proton and carbon chemical shifts Melting points were measured on an X 6 melting point apparatus and were uncorrected Optical rotations were measured on a Perkin Elmer 343 polarimeter and mass spectra were obtained with a TRACE MS spectrometer Elemental analyses were performed on a Vario EL elemental analyzer Enantiomeric excesses were determined by gas chromatography with an FID detector using chiral column SGE CYCLODEX 25 m 0 25 mm i d on a Varian CP 3800 instrument General procedure for the preparation of chiral azetidines from S 1 4 methoxyphenyl ethylamine The synthesis of 1 1 4 methoxyphenyl ethyl 2 phenyl 3hydroxylazetidine L1 is representative Anhydrous MgSO4 4 8 g 40 mmol was added to a CH2 Cl2 60 ml solution of benzaldehyde 2 14 g 20 mmol and S 1 4 methoxyphenyl ethylamine 3 02 g 20 mmol at room temperature After



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