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手性助剂诱导下的α,β-不饱和酮的不对称加氢反应及其在合成(R)-麝香酮中的应用 被引量:3

Asymmetric Hydrogenation of α,β Unsaturated Ketones in the Presence of Chiral Auxiliaries—Preparation of ( R ) Muscone
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摘要 在THF溶液中,40-60℃及0.3-0.5MPa氢压条件下,[RuCl2(cht)]2+(S)-BINAP手性催化剂体系催化不饱和手性缩酮2选择加氢,再经脱去手性二醇,即可高立体选择性地制得(R)-3-甲基环十五烷酮(4,(R)-(-)-麝香酮),化学收率≥95%,光学纯度≥97%.手性缩酮2由D-苏糖醇或D-葡萄糖衍生的手性二醇3与3-甲基环十五烯-2-酮1生成. Asymmetric hydrogenation of α,β unsaturated ketones is a great challenge to synthetic chemists. In this paper a novel process was presented. Chiral alcohols ( 3 ) from tartaric acid or glucose react with 3 methyl 2 cyclopentadecen 1 one ( 1 ) to form unsaturated chiral ketal ( 2 ). In the presence of another chiral catalysts, like [RuCl 2(cht)] 2 [( S ) BINAP], hydrogenation of the chiral ketals ( 2 ) produces, after the release of chiral alcohol, ( R ) muscone with high optical yield (98% e.e.) and good chemical yield (97%) under the conditions of THF, 50℃, 0.3 MPa for 40 h.
出处 《分子催化》 EI CAS CSCD 北大核心 1997年第6期433-438,共6页 Journal of Molecular Catalysis(China)
关键词 不饱和酮 不对称氢化 (R)-麝香酮 麝香酮 Double asymmetric induction α β unsaturated ketone Asymmetric hydrogenation ( R ) muscone
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