新的手性NOBIN催化剂的合成及L-异亮氨酸催化醛酮的不对称羟醛缩合反应的研究
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摘要
手性硫脲及其衍生物是各种亲核试剂对亚胺、醛、缺电子烯烃加成反应的非常有效的有机催化剂之一。本研究以手性NOBIN出发,经过拆分、乙酰化、酯水解、成醚、酰胺水解、异硫氰化、成脲等11步反应合成出一个以NOBIN为骨架的具有C2对称轴的手性有机小分子硫脲催化剂16,通过1H NMR、13C NMR谱以及X-单晶衍射对反应中间体(R)-15及最终产物16进行结构表征,表明目前尚无报道合成此催化剂。并利用催化剂16对醛的不对称膦氢化反应、醛的不对称氢氰化反应以及硝基烯的迈克尔加成反应进行催化研究。在催化硝基烯与丙二酸二甲酯的不对称迈克尔加成反应中得到催化产物19,为NOBIN衍生的硫脲催化剂催化硝基烯的不对称迈克尔加成反应的研究起了一定的探索并提供一定的研究价值。
某些简单的天然有机小分子也可以作为催化剂,如L-脯氨酸可以催化羟醛缩合反应、Mannich反应以及共轭反应等。本研究选L-异亮氨酸为催化剂,以环戊酮、环己酮和一系列取代苯甲醛作为底物进行催化不对称羟醛缩合反应的研究并获得9个羟醛产品(化合物23—化合物31)。经1H NMR确定结构,高效液相色谱测定其对映选择性,获得最高为99%的对映选择性。因此,本研究开发出以L-异氨基酸在水介质中催化羟醛缩合反应的方法,这种方法能有效避免有机溶剂对环境的污染,并且能达到催化效率高、对映选择性好的特点。
Chiral thiourea and its derivatives are the most effective catalysts for catalyticing addition reaction of various nucleophiles reacte with imine, aldehyde and so on. A new thiourea catalyst 16 which was derived from chiral NOBIN was synthesized by 11 steps and characterized by 1H NMR, 13C NMR and single-crystal X-ray analysis. Then it was used as a catalyst to catalytic asymmetric reaction of phospine hydrogenation of aldehydes, asymmetric reaction of hydrogen cyanide of aldehydes, asymmetric reaction of Michael addition of nitroene. As it was use in catalysting asymmetric reaction of Michael addition of nitroene, we abtained compound 19. The research can give us a helpful message to study on this point.
Recent studies show that some of the simple natural organic molecules can be used as catalysts. Such as L-proline can be used to catalytic asymmetric Aldol reactions. We decided to use L-isoleucine as a catalyst and used it to catalytic asymmetric Aldol reactions in aqueous media, so that to find a widely used way of catalyticing high diastereo- and enantioselectivities Aldol reaction that can be avoid to use organic solvents.
某些简单的天然有机小分子也可以作为催化剂,如L-脯氨酸可以催化羟醛缩合反应、Mannich反应以及共轭反应等。本研究选L-异亮氨酸为催化剂,以环戊酮、环己酮和一系列取代苯甲醛作为底物进行催化不对称羟醛缩合反应的研究并获得9个羟醛产品(化合物23—化合物31)。经1H NMR确定结构,高效液相色谱测定其对映选择性,获得最高为99%的对映选择性。因此,本研究开发出以L-异氨基酸在水介质中催化羟醛缩合反应的方法,这种方法能有效避免有机溶剂对环境的污染,并且能达到催化效率高、对映选择性好的特点。
Chiral thiourea and its derivatives are the most effective catalysts for catalyticing addition reaction of various nucleophiles reacte with imine, aldehyde and so on. A new thiourea catalyst 16 which was derived from chiral NOBIN was synthesized by 11 steps and characterized by 1H NMR, 13C NMR and single-crystal X-ray analysis. Then it was used as a catalyst to catalytic asymmetric reaction of phospine hydrogenation of aldehydes, asymmetric reaction of hydrogen cyanide of aldehydes, asymmetric reaction of Michael addition of nitroene. As it was use in catalysting asymmetric reaction of Michael addition of nitroene, we abtained compound 19. The research can give us a helpful message to study on this point.
Recent studies show that some of the simple natural organic molecules can be used as catalysts. Such as L-proline can be used to catalytic asymmetric Aldol reactions. We decided to use L-isoleucine as a catalyst and used it to catalytic asymmetric Aldol reactions in aqueous media, so that to find a widely used way of catalyticing high diastereo- and enantioselectivities Aldol reaction that can be avoid to use organic solvents.
引文
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