A New Entry to Enantioselective Synthesis of α-Nethylene-β-hydroxy Ketones by the Chalcogeno-Baylis-Hillman Reaciton

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概要

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• Chiral hydroxy chalcogenides in the presence of TiCl_4 achieved the asymmetric version of the chalcogeno-Baylis-Hillman reaction. The reaction proceeded under atmospheric pressure for 1h. 10-Methylthioisoborneol (9) achieved the best enantioselectivity. A methoxy derivative 10 of 10-methylthioisoborneol resulted in lower-selectivity than that obtained by 10-methylthioisoborneol (9). A hydroxyl group is required to perform good asymmetric induction. The asymmetric chalcogeno-Baylis-Hillman reaction with a C_2 symmetric bidentate ligand-TiCl_4 complex was also examined. Diol ligands gave the adduct in low to good yields with low or no enantiomeric excess. The adduct was also obtained in low to high yields with low or no enantiomeric excess using bisoxazoline ligands.

• 公益社団法人日本薬学会の論文
• 1999-07-15

著者

• 渡辺 真一

  岐阜薬科大学

• Iwama Tetsuo

  Gifu Pharmaceutical University

• KATAOKA Tadashi

  Gifu Pharmaceutical University

• Iwamura T

  Gifu Pharmaceutical Univ. Gifu Jpn

• Iwamura Tatsunori

  Gifu Pharmaceutical University

• TSUJIYAMA Shin-ichiro

  Gifu Pharmaceutical University

• KINOSHITA Hironori

  Gifu Pharmaceutical University

• KANEMATSU Kiyoko

  Gifu Pharmaceutical University

• TSURUKAMI Yasuo

  Gifu Pharmaceutical University

• WATANABE Shin-ichi

  Gifu Pharmaceutical University

• Iwama T

  Gifu Pharmaceutical University

• Iwamura Tatsunori

  Gifu Pharmaceutical Univ. Gifu Jpn

• Kataoka T

  Gifu Pharmaceutical Univ. Gifu Jpn

• Tsujiyama Shinichiro

  Gifu Pharmaceutical University

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