基于氢键活化的不对称有机催化的硫醚氧化和phospha-Michael加成反应研究
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摘要
本文基于“氢键活化”的概念，以手性的联萘酚（BINOL），金鸡纳碱，1,2-环己二胺，1,2-二苯基乙二胺（DPEN）为原料，合成了一系列氢键供体型有机小分子催化剂。系统研究了手性磷酸催化的不对称硫醚氧化反应以及手性硫脲催化的不对称phospha-Michael加成反应，探索了有机小分子对亚磷酸酯与苯亚甲基丙二腈的不对称phospha-Michael加成反应的催化性能。
论文的第一部分工作，我们以(R)-BINOL为原料，合成了一系列手性磷酸催化剂，实现了手性磷酸催化的芳基烷基硫醚和芳醛衍生的双缩硫醛的不对称氧化反应，以双氧水为氧化剂，反应分别能以中等到良好的收率（35–92%）和良好的对映选择性（83:17–91:9er）得到手性芳基烷基亚砜，以良好到优秀的收率（60–99%）、优秀的非对映选择性（up to>99:1）和良好的对映选择性（78:22–87:13er）得到缩硫醛单氧化物。反应过程中无其他副产物生成。同时，我们通过实验证明本反应为直接磺氧化反应，不存在亚砜过氧化导致的动力学拆分过程。
第二部分工作中，我们以金鸡纳碱和DPEN为原料合成了一系列叔胺硫脲型催化剂，成功实现了手性硫脲催化的亚磷酸二烷基酯对靛红丙二腈缩合物的不对称phospha-Michael加成反应。优化条件下，反应能以良好到优秀的收率（78–98%）以及良好到优秀的对映选择性（64–95%ee）得到亚磷酸酯与不饱和丙二腈的加成产物。在本方法中，不需要氮保护的靛红丙二腈底物的活性和对映选择性最高，避免了这类底物通常需要的保护和脱保护的步骤，具有较高的应用价值。
本论文的第三部分工作，我们首先合成了四种手性方酰胺催化剂，之后以苯亚甲基丙二腈作为不对称phospha-Michael加成反应的底物，探索了几种有机小分子催化剂对亚磷酸酯作为磷亲核试剂的催化性能。实验结果表明，常见的氢键给体型催化剂不能高对映选择性地催化本反应。我们将继续寻找适于小分子催化的不对称phospha-Michael加成体系。
Hydrogen bonding to an electrophile serves to decrease the electron density of thisspecies, activating it toward nucleophilic attack. Some small molecule chiralhydrogen-bond donors were prepared following the reported procedures, which havebeen successfully applied to promoting the asymmetric phospha-Michael addition ofdiethyl phosphites to isatylidenemalononitriles and asymmetric oxidation of aryl alkylsulfides and aldehyde-derived1,3-dithianes.
In the first part,(R)-BINOL derived chiral phosphoric acids have been explored asorganocatalysts for the asymmetric oxidation of a series of aryl alkyl sulfides and1,3-dithianes derived from aldehydes with aqueous H2O2as the terminal oxidant. Theenantiomerically enriched sulfoxides are obtained in moderate to excellent yield (up to99%) with excellent diastereoselectivity (up to>99:1dr) and moderate to goodenantioselectivity (up to91:9er). In particular, the present protocol stereoselectivelyprovides an efficient access to enantiomerically enriched aryl alkyl sulfoxides anddithioacetal mono-sulfoxides, which sternly restrains the formation of the undesirablebyproducts of sulfones or disulfoxides. The tracking experiments also verify that thisapproach proceeds via a direct sulfoxidation process, instead of a kinetic resolutionroute by overoxidation of the resulting sulfoxides.
α-Functionalized phosphonic acids are valuable intermediates for the preparationof medicinal compounds and synthetic intermediates. An unprecedented and highlyenantioselective organocatalytic synthesis of dialkyl3-(dicyanomethyl)-2-oxoindolin-3-ylphosphonate was achieved through an asymmetric conjugate addition of diethylphosphites to isatylidenemalononitriles catalyzed by DPEN-based bifunctional thiourea.Optically active products bearing quaternary chiral carbon stereocenters were obtainedin high yields (78–98%) with good to excellent enantioselectivities (up to95%ee).Masking of the "N"(e.g., Me-) led to dramatic decrease of the ee values and yields.
Four chiral squaramides were synthesized using simple methods. Their catalyticeffects on the asymmetric addition of diethyl phosphite to benzylidenemalononitrilewere evaluated, and it was found that they could promote the reaction with only23%ee.Investigations are still ongoing in our laboratory to utilize other optically smallmolecule as catalysts for this asymmetric transformation.
论文的第一部分工作，我们以(R)-BINOL为原料，合成了一系列手性磷酸催化剂，实现了手性磷酸催化的芳基烷基硫醚和芳醛衍生的双缩硫醛的不对称氧化反应，以双氧水为氧化剂，反应分别能以中等到良好的收率（35–92%）和良好的对映选择性（83:17–91:9er）得到手性芳基烷基亚砜，以良好到优秀的收率（60–99%）、优秀的非对映选择性（up to>99:1）和良好的对映选择性（78:22–87:13er）得到缩硫醛单氧化物。反应过程中无其他副产物生成。同时，我们通过实验证明本反应为直接磺氧化反应，不存在亚砜过氧化导致的动力学拆分过程。
第二部分工作中，我们以金鸡纳碱和DPEN为原料合成了一系列叔胺硫脲型催化剂，成功实现了手性硫脲催化的亚磷酸二烷基酯对靛红丙二腈缩合物的不对称phospha-Michael加成反应。优化条件下，反应能以良好到优秀的收率（78–98%）以及良好到优秀的对映选择性（64–95%ee）得到亚磷酸酯与不饱和丙二腈的加成产物。在本方法中，不需要氮保护的靛红丙二腈底物的活性和对映选择性最高，避免了这类底物通常需要的保护和脱保护的步骤，具有较高的应用价值。
本论文的第三部分工作，我们首先合成了四种手性方酰胺催化剂，之后以苯亚甲基丙二腈作为不对称phospha-Michael加成反应的底物，探索了几种有机小分子催化剂对亚磷酸酯作为磷亲核试剂的催化性能。实验结果表明，常见的氢键给体型催化剂不能高对映选择性地催化本反应。我们将继续寻找适于小分子催化的不对称phospha-Michael加成体系。
Hydrogen bonding to an electrophile serves to decrease the electron density of thisspecies, activating it toward nucleophilic attack. Some small molecule chiralhydrogen-bond donors were prepared following the reported procedures, which havebeen successfully applied to promoting the asymmetric phospha-Michael addition ofdiethyl phosphites to isatylidenemalononitriles and asymmetric oxidation of aryl alkylsulfides and aldehyde-derived1,3-dithianes.
In the first part,(R)-BINOL derived chiral phosphoric acids have been explored asorganocatalysts for the asymmetric oxidation of a series of aryl alkyl sulfides and1,3-dithianes derived from aldehydes with aqueous H2O2as the terminal oxidant. Theenantiomerically enriched sulfoxides are obtained in moderate to excellent yield (up to99%) with excellent diastereoselectivity (up to>99:1dr) and moderate to goodenantioselectivity (up to91:9er). In particular, the present protocol stereoselectivelyprovides an efficient access to enantiomerically enriched aryl alkyl sulfoxides anddithioacetal mono-sulfoxides, which sternly restrains the formation of the undesirablebyproducts of sulfones or disulfoxides. The tracking experiments also verify that thisapproach proceeds via a direct sulfoxidation process, instead of a kinetic resolutionroute by overoxidation of the resulting sulfoxides.
α-Functionalized phosphonic acids are valuable intermediates for the preparationof medicinal compounds and synthetic intermediates. An unprecedented and highlyenantioselective organocatalytic synthesis of dialkyl3-(dicyanomethyl)-2-oxoindolin-3-ylphosphonate was achieved through an asymmetric conjugate addition of diethylphosphites to isatylidenemalononitriles catalyzed by DPEN-based bifunctional thiourea.Optically active products bearing quaternary chiral carbon stereocenters were obtainedin high yields (78–98%) with good to excellent enantioselectivities (up to95%ee).Masking of the "N"(e.g., Me-) led to dramatic decrease of the ee values and yields.
Four chiral squaramides were synthesized using simple methods. Their catalyticeffects on the asymmetric addition of diethyl phosphite to benzylidenemalononitrilewere evaluated, and it was found that they could promote the reaction with only23%ee.Investigations are still ongoing in our laboratory to utilize other optically smallmolecule as catalysts for this asymmetric transformation.
引文
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