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Synlett 2000; 2000(2): 239-241
DOI: 10.1055/s-2000-6510
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Novel C 2-Symmetric Chiral Oxazolinyl Biaryl Ligands Bearing a Hydroxyl Group

Yoshitane Imai* , Shigeaki Matsuo, Wanbin Zhang, Yohji Nakatsuji, Isao Ikeda
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan; Fax +81-6-68 79-73 59; E-mail: ikeda@ap.chem.eng.osaka-u.ac.jp
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Publikationsdatum:
31. Dezember 2000 (online)

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Novel C 2-symmetric bisoxazoline ligands 4 and 5 having an axis-fixed and -unfixed biaryl backbone, respectively, and a hydroxyl group in the substituent of the oxazoline ring, were prepared from biaryl dicarboxylic acids and l-serine methyl ester hydrochloride through the corresponding bisoxazolines 7 and the biphenyl derivative bearing a methoxycarbonyl substituent as the intermediate. With these ligands, up to 88% ee was afforded for the asymmetric alkylation of benzaldehyde with diethylzinc.

multi-chirality - oxazoline - axial chirality - asymmetric alkylation - diethyl zinc