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化学学报
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化学学报 ›› 2007, Vol. 65 ›› Issue (6): 553-556. 上一篇    下一篇

研究论文

新颖有机催化剂的合成及催化不对称直接Aldol反应研究

郑吉富, 李耀先, 张锁秦*, 王小明, 杨松涛, 白杰, 王芳, 张广良, 刘福安   

  1. (吉林大学化学学院 长春 130023)
  • 投稿日期:2006-05-17 修回日期:2006-08-08 发布日期:2007-03-28
  • 通讯作者: 张锁秦

Studies on Synthesis of Novel Chiral Organocatalysts and Its Evaluations for Asymmetric Direct Aldol Reactions

ZHENG Ji-Fu; LI Yao-Xian; ZHANG Suo-Qin*; WANG Xiao-Ming; YANG Song-Tao; BAI Jie; WANG Fang; ZHANG Guang-Liang; LIU Fu-An   

  1. (College of Chemistry, Jilin University, Changchun 130023)
  • Received:2006-05-17 Revised:2006-08-08 Published:2007-03-28
  • Contact: ZHANG Suo-Qin

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被引次数

9 | 1

以N-苄氧羰基-(S)-脯氨酸和5-(1-氨基烷基)四氮唑(烷基: 甲基、乙基、2-苯基乙基)为原料, 经两步反应合成了3个新颖的有机催化剂: (S)-5-脯氨酰胺基甲基四氮唑(3a), (S,S)-5-(1-脯氨酰胺基乙基)四氮唑(3b)和(S,S)-5-(1-脯氨酰胺 基-2-苯基乙基)四氮唑(3c), 并首次将其用于催化丙酮和含吸电子基芳香醛的不对称直接aldol反应. 在室温条件下, 催化剂3b表现出较好的催化活性, 产物的ee值最高可达96%.

关键词: 有机催化剂, 不对称催化, 直接aldol反应, 脯氨酰胺衍生物

Three novel organocatalysts (S)-5-prolylaminomethyltetrazole (3a), (S,S)-5-(1-prolylaminoethyl) tetrazole (3b) and (S,S)-5-(1-prolylamino-2-phenylethyl)tetrazole (3c) were readily prepared from N-benzyloxycarbonyl-(S)-proline and corresponding 5-(1-aminoalkyl)tetrazol (alkyl: methyl, ethyl and 2-phenylethyl) by the known reaction sequences in just two steps. Their catalytic per-formances were first evaluated in the asymmetric direct aldol reactions of acetone with electron-deficient aromatic aldehydes. At room temperature, the catalyst 3b displayed the efficient reactivity and the enantiomeric excess (ee) value of the products was up to 96%.

Key words: organocatalyst, asymmetric catalysis, direct aldol reaction, prolinamide derivative