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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (05): 567-569. 上一篇    下一篇

研究论文

N-[(S)-脯氨酰]羟胺的合成及催化直接不对称羟醛反应研究

丁一1，张雅文1，刘艳华1，罗晓清2，马济美1，沈宗旋*,1   

  1. 1苏州大学化学化工学院江苏省有机合成重点实验室 苏州 215006)
    (2苏州卫生学校 苏州 215007)
  • 收稿日期:2004-09-13 修回日期:2004-12-06 发布日期:2004-04-30
  • 通讯作者: 沈宗旋

Synthesis of N-(S)-Prolylhydroxylamine and Its Cataly-sis in Direct Asymmetric Aldol Reactions

DING Yi1,ZHANG Ya-Wen1,LIU Yan-Hua1,LUO Xiao-Qing2
MA Ji-Mei1,SHEN Zong-Xuan*,1   

  1. (1 Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering,
    Suzhou University, Suzhou 215006)
    (2 Suzhou Health School, Suzhou 215007)
  • Received:2004-09-13 Revised:2004-12-06 Published:2004-04-30
  • Contact: SHEN Zong-Xuan

PDF

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(S)-脯氨酸用苯甲氧羰酰氯保护氨基后用混合酸酐法与羟胺偶合, 给出N-[N-苯甲氧羰酰-(S)-脯氨酰]羟胺, 催化氢解脱去保护基得标题化合物. 该化合物对映选择性催化直接羟醛反应, 产率最高达到90.0%, 对映体过量最高达89.5%.

关键词: 直接不对称羟醛反应, 手性催化剂, (S)-脯氨酰羟胺

(S)-Proline was N-protected using phenylmethoxycarbonyl chloride and then coupled with hydroxylamine by the method of mixed anhydride, giving N-[N-phenylmethoxycarbonyl-(S)-prolyl]-hydroxylamine, which, after deprotection by catalytic hydrogenolysis, afforded the title compound. This compound efficiently catalyzed the direct asymmetric aldol reaction with the yield up to 90.0% and enantiomeric excess up to 89.5%.

Key words: chiral catalyst, direct asymmetric aldol reaction, N-(S)-prolylhydroxylamine