手性金属络合物催化的不对称1,3-偶极环加成和Mukaiyama-Mannich加成反应
发布时间：2018-10-19 15:13
【摘要】：发展新的有机合成方法能够为医药、农药、材料和精细化工品的研发提供简便而有效的途径。探索廉价高效的催化剂以及温和的反应条件,实现碳-碳键、碳-氮键和其它碳-杂原子键的构建,进而完成复杂分子的合成,是有机化学的研究主题之一。本论文工作主要围绕以下反应进行:1.通过缺电子烯烃和硝酮参与的不对称1,3-偶极环加成反应制备手性异VA唑烷类化合物;2.苯并磺内酰亚胺和烯醇硅醚的不对称Mukaiyama-Mannich反应实现含季碳中心的苯并磺酰胺类衍生物的制备;3.探索出通过钯催化的构建烯基Csp2-P键的方式合成α,β-不饱和烯基膦化物的方法。研究了 α,β-不饱和酰基羧酸酯和硝酮参与的不对称1,3-偶极环加成反应,以中等以上的收率,高非对映选择性和对映选择性地得到含三个相邻手性中心的异VA唑烷类化合物。该反应运用了少有报道的可双齿配位的联羰型缺电子烯烃为亲偶极体,与金属络合物以1,4-位配位的形式形成五元环反应中间体,进而降低缺电子烯烃的HOMO能量而活化底物。该部分工作进一步丰富了 α,β-不饱和酰基羧酸酯的C=C体系所参与的反应类型。发展了一种制备手性2,3-位芳基(烷基)取代4-位酯基取代的异VA唑烷类化合物的新方法,该反应使用Cu(Ⅱ)-Inda-BOX为催化剂,在0℃条件下催化α,β-不饱和酰基膦酸酯和硝酮的环加成,以良好的收率得到环化产物,并获得唯一的区域选择性、优异的非对映选择性和对映选择性。该反应在温和的条件下得到含三个相邻手性中心的异VA唑烷类化合物,同时膦酸酯具有易衍生化的优点。研究了芳香酮衍生的烯醇硅醚和环状N-磺酰基亚胺酯的不对称Mukaiyama-Marmich加成反应。在优化的反应条件下(2-10 mol%的Ni(ClO4)·6H2O-双VA唑啉,在0℃或室温条件下,CHCl3为溶剂),以高收率(89-99%)和高对映选择性(84-99%ee)得到一系列不同取代的含手性季碳中心的苯并磺内酰胺类化合物。该方法能够拓展到远端的共轭体系和有空间位阻的烯醇硅醚,同样取得了优异的催化结果。Mannich加成产物可以方便地转化为吖啶类或新骨架的多元环状苯并磺内酰胺类化合物。发展了钯催化的α-位连有吸电子基团的卤代烯烃和二苯基膦的偶联反应,并完成了系列新型的芳甲叉基膦氧配体的制备。该合成策略可作为构建新型的烯基Csp2-P键的补充方案,更进一步,可将烯基膦化物产物应用到不同类型的反应中以考察其潜在的配位作用和催化性能。
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【学位授予单位】：中国农业大学
【学位级别】：博士
【学位授予年份】：2017
【分类号】：O621.251
本文编号：2281516
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【学位授予单位】：中国农业大学
【学位级别】：博士
【学位授予年份】：2017
【分类号】：O621.251
【参考文献】
相关期刊论文 前5条
1 刘迅绅;李美美;由君;刘波;;Ni-DBFOX/Ph催化N-α,β-不饱和酰基吡唑与C,N-二芳基硝酮的不对称1,3-偶极环加成反应[J];有机化学;2017年01期
2 彭静;陈俐;马敏;;环磷腺苷葡胺联合培哚普利治疗慢性心力衰竭的效果[J];中国医药导报;2015年34期
3 刘刚;;啶菌VA唑对韭菜灰霉病防效较高并且稳定[J];农药市场信息;2014年07期
4 倪凤林;陆致平;;啶菌VA唑防治番茄灰霉病效果好[J];农药市场信息;2012年07期
5 程春生;;高效杀菌剂啶菌VA唑的创制及其产业化[J];农药市场信息;2006年03期
，本文编号：2281516
本文链接：https://www.wllwen.com/kejilunwen/huaxue/2281516.html
教材专著
