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手性氨基醇促进烯丙基三氯硅烷和酰腙的不对称烯丙基化反应
引用本文:华远照,闫云辉,程迪,郭伟,王敏灿.手性氨基醇促进烯丙基三氯硅烷和酰腙的不对称烯丙基化反应[J].新乡医学院学报,2010,27(2).
作者姓名:华远照  闫云辉  程迪  郭伟  王敏灿
作者单位:1. 新乡医学院化学教研室,河南新乡,453003
2. 郑州大学化学系,河南郑州,450052
摘    要:目的研究手性氨基醇在酰腙不对称烯丙基化反应中的促进作用。方法烯丙基三氯硅烷和酰腙在化合物Ⅰ(1S,2S)-1-(对硝基苯基)-2-(3,4甲-叉二氧基苯甲胺基)-1,3丙-二醇]的作用下进行烯丙基化加成反应,产物的对映体过量值利用高效液相色谱检测。结果手性氨基醇配体化合物Ⅰ能够促进烯丙基三氯硅烷和酰腙的烯丙基化加成反应,在它的辅助作用下,烯丙基化加成产物的产率可达到57%,对映体过量值最高达到22%。温度可影响产率,反应在0~15℃条件下进行较为合适。结论首次将手性化合物Ⅰ应用于烯丙基三氯硅烷和酰腙的烯丙基化加成反应中,结果表明化合物Ⅰ能够促进该反应的发生。

关 键 词:烯丙基化  酰腙  手性  不对称

Asymmetric allylation of acylhydrazones with allyltrichlorosilane under a chiral aminoalcohol
HUA Yuan-zhao,YAN Yun-hui,CHENG Di,GUO Wei,WANG Min-can.Asymmetric allylation of acylhydrazones with allyltrichlorosilane under a chiral aminoalcohol[J].Journal of Xinxiang Medical College,2010,27(2).
Authors:HUA Yuan-zhao  YAN Yun-hui  CHENG Di  GUO Wei  WANG Min-can
Abstract:Objective To research the effects of a chiral aminoalcohol in the asymmetric allylation of acylhydrazones.Methods The asymmetric allylation of acylhydrazones with allyltrichlorosilane under the stoichiometric amounts of(1S,2S)-1-(p-nitrophenyl)-2-(3′,4′-methylenedioxabenzylamino) propane-1,3-diol(compoundⅠ) was carried out and the enantioselective excess(e.e.) value of productions were detected by high performance liquid chromatography.Results The chiral aminoalcohol ligand compound Ⅰcan promote the asymmetric allylation of acylhydrazones and the yield was 57%;The highest values of e.e.obtained for this reaction was 22%.Temperature can affect the yield,reaction in 0 ~ 15 ℃conditions are relatively appropriate.Conclusion Chiral compounds Ⅰ for the first time was applied to allylation of acylhydrazones with allyltrichlorosilane and the results showed that the compound Ⅰ can contribute to the occurrence of the reaction.
Keywords:allylation  acylhydrazone  ahirality  asymmetry
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