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新型手性双功能有机催化剂的合成及其催化不对称Henry反应合成(R)-aegeline 被引量：1

Synthesis of a Novel Chiral Bifunctional Organo-catalyst and Its Catalytic Asymmetric Henry Reaction to Synthesize (R)-aegeline
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摘要 以(S)-2-氨甲基-1-乙基吡咯烷为原料,合成了新型手性双功能有机催化剂(S)-1-[3,5-二(三氟甲基)苯基]-3-(1-乙基吡咯烷基-2-甲基)硫脲(2,产率82.2%)。用2催化对甲氧基苯甲醛与硝基甲烷的不对称Henry反应,制得(R)-1-(4-甲氧基苯基)-2-硝基乙醇(3,84%ee);3经Pd/C催化氢化得到(R)-2-氨基-1-(4-甲氧基苯基)乙醇(4);4与反式肉桂酰氯反应合成了(R)-aegeline,总产率37.6%(以对甲氧基苯甲醛计)。化合物的结构经1HNMR,13CNMR和MS表征。 A novel chiral bifunctional organo-catalyst- （S） -1 -[ 3,5-bis （ trifluoromethyl ） phenyl ] - 3 - （ 1 -ethylpyrrolidin -2-methyl ） thiourea （ 2 ） was synthesized from （ S ） -2-aminomethyl- 1 -ethylpyrrolidine. 2 was applied in the asymmetric Henry reaction of 4-methoxybenzaldehyde with nitromethane to afford （R） -1 -（4-methoxyphenyl） -2-nitroethanol（3） in 84% ee. By Pd/C-catalyzed hydrogenation, 3 was converted into （R） -2-amino-1-（4-methoxyphenyl） ethanol（4）, which was treated with （E） -cinnamoyl chloride to give （R）-aegeline. The overall yield from 4-methoxybenzaldehyde was 37.6%.
作者 宿亮 匡永清 杨昊宇 向顺 孟丽丽 谢斌
机构地区 湖南大学化学化工学院
出处 《合成化学》 CAS CSCD 北大核心 2009年第4期444-446,449,共4页 Chinese Journal of Synthetic Chemistry
基金 湖南省自然科学基金资助项目(09JJ5007)
关键词 手性有机催化剂 不对称HENRY反应 (R)-aegeline β-硝基醇 Β-氨基醇 合成 chiral organo-catalyst asymmetric Henry reaction （R） -aegeline synthesis
分类号 R914.5 [医药卫生—药物化学] O621.3 [理学—有机化学]
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参考文献13

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合成化学
2009年 第4期

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