Asymmetric synthesis by the intramolecular haloetherification reaction of ene acetal: discrimination of prochiral dienes in cyclohexane systems.

  title={Asymmetric synthesis by the intramolecular haloetherification reaction of ene acetal: discrimination of prochiral dienes in cyclohexane systems.},
  author={Hiromichi Fujioka and Naoyuki Kotoku and Yoshinari Sawama and Hidetoshi Kitagawa and Yusuke Ohba and Tsung-Lung Wang and Yasushi Nagatomi and Yasuyuki Kita},
  journal={Chemical \& pharmaceutical bulletin},
  volume={53 8},
A novel asymmetric synthesis of the cyclohexane derivative functionalized by some substituents has been developed from the diene acetals (1), prepared from the corresponding diene aldehyde and (+)-hydrobenzoin. The treatment of 1 with NBS in the presence of MeOCH2CH2OH predominantly afforded 2 in a stereoselective manner. Subsequent alkylation of the methoxyethoxy group produced the optically active cyclohexene compounds (3) in good yields. The stereoselective chemical modification of the… Expand
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