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DOI: https://doi.org/10.6023/cjoc1111252

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 ,
  • 叶仲斌 ,
  • 蔡潇潇 ,
  • 刘曼 ,
  • 蒋文超
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  • 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

  网络出版日期: 2012-02-17

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.

收起

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

  • Gou Shaohua ,
  • Ye Zhongbin ,
  • Cai Xiaoxiao ,
  • Liu Man ,
  • Jiang Wenchao
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  • 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 date: 2011-11-25

  Revised date: 2011-12-30

  Online 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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摘要

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

本文引用格式

苟绍华 , 叶仲斌 , 蔡潇潇 , 刘曼 , 蒋文超 . 手性氨基酸酰胺催化二乙基锌与芳香醛不对称加成反应[J]. 有机化学, 0 , 0(0) : 1136 -1140 . DOI: 10.6023/cjoc1111252

Abstract

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

参考文献

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