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α-和β-硅基烯基镁化物在高选择性合成反应中的应用
Applications of α-and β-Silylvinyl Grignard Reagents in Highly Selective Synthetic Reactions
【作者】 周舟;
【导师】 蔡明中;
【作者基本信息】 江西师范大学 , 有机化学, 2006, 硕士
【摘要】 本论文研究了(Z)-α-硅基烯基Grignard试剂在Pd(PPh3)4催化下与(E)-α-碘代烯基锡烷的交叉偶联反应,为立体选择合成(Z,Z)-2-硅基-3-锡基-1,3-二烯提供了方便方法。 研究了(E)-β-硅基烯基Grignard试剂在高选择性合成反应中的应用。按文献方法,经芳基硅基乙炔的镁氢化反应制备了(E)-β-硅基烯基Grignard试剂。通过(E)-β-硅基烯基Grignard试剂与醛或酮的加成反应,提供了立体选择合成(2E)-3-硅基烯丙醇的简便方法。研究了(E)-β-硅基烯基Grignard试剂与三烃基氯化锡的反应,提供了立体选择合成(E)-β-硅基烯基锡烷的新方法。
【Abstract】 In this dissertation we studied (Z)-α-silylvinyl Grignard reagents and (E)-α-iodovinylstannanes underwent a cross-coupling reaction in the presence of Pd(PPh3)4 catalyst to afford stereoselectively the difunctionalized 1,3-dienes containing silicon ang tin in good yields.We also studied the application of (E)-β-silylvinyl Grignard reagents in highly selective synthetic reactions. According to the literature procedure, (E)-β-silylvinyl Grignard reagents were prepared by hydromagnesiation of 1-aryl-2-silylacetylenes.We provided a facile route stereoselective synthesis of (2E)-3-silyl substituted allylic alcohols by the reaction of (E)-β-silylvinyl Grignard reagents with aldehydes or ketones. We also studied the reaction of (E)-β-silylvinyl Grignard reagents with trialkylstannyl chlorides in diethyl ether, which provided a new method for the stereoselective synthesis of (E)-β-silylvinylstannanes.
【Key words】 hydromagnesiation; Grignard reagents; stereoselective synthesis; cross-coupling reaction; palladium catalysis; (E)-α-iodovinylstannane; silylarylacetylene; (E)-allylic alcohol; (E)-β-silylvinylstannane;
- 【网络出版投稿人】 江西师范大学 【网络出版年期】2006年 12期
- 【分类号】O621.25
- 【下载频次】42