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Synlett 2001; 2001(5): 0709-0711
DOI: 10.1055/s-2001-13385
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Scandium(III) Triflate/Isopropyl-Pybox Complex as an Efficient Catalyst for Asymmetric Diels-Alder Reaction

Shin-ichi Fukuzawa* , Hiroshi Matsuzawa, Ken Metoki
  • *Department of Applied Chemistry, Institute of Science and Engineering, Chuo University, Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan; Fax 81-(0)3-3817-1895; E-mail: fukuzawa@chem.chuo-u.ac.jp
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Publication Date:
31 December 2001 (online)

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The chiral scandium(III) triflate/i-Pr-pybox complex efficiently catalyzes the asymmetric Diels-Alder reaction of 1,3-dienes with acyl-1,3-oxazolidin-2-ones (1 a - c) afford the corresponding adducts in good yields with up to 90% ee. The reaction can be carried out in less toxic benzotrifluoride and supercritical carbon dioxide while remaining good selectivity (65-75% ee).

scandium - asymmetric catalysis - asymmetric synthesis - Diels-Alder reactions - cycloadditions - supercritical carbon dioxide