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有机化学
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有机化学 ›› 2012, Vol. 32 ›› Issue (06): 1136-1140.DOI: 10.6023/cjoc1111252 上一篇    下一篇

研究简报

手性氨基酸酰胺催化二乙基锌与芳香醛不对称加成反应

苟绍华a,b, 叶仲斌a,b, 蔡潇潇b, 刘曼b, 蒋文超b   

  1. a 西南石油大学油气藏地质及开发工程国家重点实验室 成都 610500;
    b 西南石油大学化学化工学院 成都 610500
  • 收稿日期:2011-11-25 修回日期:2011-12-30 发布日期:2012-02-17
  • 通讯作者: 苟绍华 E-mail:shaohuagou@swpu.edu.cn, shgou@126.com
  • 基金资助:

    油气藏地质及开发工程国家重点实验室开放基金(No. PLN1105)资助项目.

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands

Gou Shaohuaa,b, Ye Zhongbina,b, Cai Xiaoxiaob, Liu Manb, Jiang Wenchaob   

  1. a State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu 610500;
    b School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500
  • Received:2011-11-25 Revised:2011-12-30 Published:2012-02-17
  • Supported by:

    Project supported by the Open Fund of Key Laboratory of Oil and Gas Reservoir Geology and Exploitation (No. PLN1105).

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被引次数

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将由磺酰化氨基酸和长链的含甲氧基官能团的胺制备的(S)-N-(4-甲氧基苯乙基)-3-苯基-2-(对甲基苯磺酰胺)丙酰胺(1d)手性配体用于催化二乙基锌与系列芳香醛对映选择性加成反应. 15 mol%该催化剂能够对含有吸电子基团、供电子基团及不同位阻的芳香醛均有较好的效果, 能够在比较温和的条件下获得高达87% ee 和中等程度的产率.

关键词: 加成反应, 醛, 氨基酸, 苯基乙胺, 二乙基锌

Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed by chiral ligand (S)-N-(4-methoxyphenethyl)-3-phenyl-2-(tosylamino)propanamide (1d), which was derivatived from a modular amino acids and long chain amine containg OMe. The catalytic system employing 15 mol% of 1d without using titanium complex was found to promote the addition of diethylzinc (ZnEt2) to a wide range of aromatic aldehydes with electron-donating and electron- withdrawing substituents, giving up to 87% ee of the corresponding secondary alcohol under mild conditions.

Key words: addition reaction, aldehyde, amino acid, phenylethanamine, ditheylzinc