不对称有机催化的碳杂键形成反应研究
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摘要
近年来,不对称有机催化得到了迅速发展,并逐渐成为继酶催化和金属催化之后又一类重要的不对称催化合成方法。此外,手性碳杂键的构建无论是对于基础方法学的研究,还是重要药物分子或者是天然产物的合成,都有着现实的指导意义和实际运用价值,也是有机化学家长期关注和研究的热点。本论文致力于不对称有机催化的碳杂键形成反应的设计和研究,主要内容分为四个部分。
第一部分,我们以脯胺醇衍生的催化剂实现了β-酮磷酯的不对称α-硫代反应,成功地构建了手性碳-硫键。0℃条件下,正己烷溶剂中考察了一系列环状β-酮磷酯与N-苯硫基邻苯二甲酰亚胺的反应情况,以较高的产率和对映选择性(upto 92% ee)获得了具有手性季碳中心的α-硫代β-酮磷酯类化合物。通过CD光谱确定了产物的绝对构型,并且根据反应结果推测了反应活化模式为分子间氢键活化机理,而非共价键机理。
第二部分,我们以金鸡钠碱衍生的手性叔胺为催化剂,实现了MBH酯衍生物与烷基硫醇的不对称取代反应,再次成功地构建手性碳-硫键。10℃条件下,1,4-二氧六环溶剂中,以优秀的产率和极高的对映选择性(up to 97%ee)获得相应的α-亚甲基-β-硫酯类化合物。我们通过单晶衍射确定了产物的绝对构型,简单的操作和广泛的底物范围使得该反应具有很强的实用前景。
第三部分,我们再次以金鸡钠碱衍生的手性叔胺为催化剂,实现了MBH酯衍生物与二苯甲酮亚胺的不对称胺化反应,成功构建手性碳-氮键。室温条件下,1,4-二氧六环溶剂中,以较高的产率和极高的对映选择性获得相应的α-亚甲基-β-胺基酯类化合物。随后我们经过一步酸化水解过程,首次高效地获得了未保护的a-亚甲基-β-胺基酯。
第四部分,我们以金鸡钠碱衍生的双官能手性胺实现了吲哚和2,2,2-三氟苯乙酮的不对称F-C烷基化反应。5℃条件下,1,2-二氯乙烷溶剂中以较好的产率和中等的对映选择性获得具有手性季碳中心和三氟甲基取代的叔醇类化合物。
In recent years, asymmetric organocatalysis is a rapidly growing field and now has been as the third general approach to the catalytic production of enantiomerically pure organic compounds between the extremes of enzymatic transformations and transition metal catalysis. Moreover, the construction of chiral carbon-heteroatom bond, either of the foundation of the research methodology, or the synthesis of important drug molecules and natural products, is of practical significance and application value, also this will be a long-term attention and research hot spot for organic chemist. This dissertation mainly focuses on the design and research of asymmetric organocatalytic carbon-heteroatom bond formation reaction, which is divided into four parts.
Part I:We have successfully developed the enantioselective sulfenylation ofβ-keto phosphonates and constructed the chiral C-S bond under the catalysis ofα,α-diaryl-L-prolinols. At 0℃, theα-sulfenylatedβ-keto phosphonates with a quaternary stereocenter were obtained in good yields and with excellent enantioselectivities (up to 92%ee) for variousβ-keto phosphonates and N-(arylthio)-phthalimides in hexane. The absolute configuration of the product was determined to be R by means of comparison of the CD spectrum. And on the basis of the results, the activation mode of the reaction may be attributed to a molecular interaction rather than a covalent bond.
PartⅡ:We have provided a highly efficient organocatalytic enantioselective C-S bond formation reaction between simple alkyl thiols and Morita-Baylis-Hillman (MBH) carbonates under the catalysis of a cinchona alkaloid derivative chiral tertiary amine. At 10℃, the optically activeα-methyleneβ-mercapto esters could be obtained in good yields with excellent enantioselectivities (up to 97%ee) for a wide range of alkyl thiols and MBH carbonates in 1,4-dioxane. And the absolute configuration of the product was determined to be S by means of an X-ray crystallographic analysis, the broad scope and simple operation makes this methodology very practical.
Part III:We have provided a highly efficient asymmetric amination reaction of Morita-Baylis-Hillman (MBH) carbonates with benzophenone imine and constructed the chiral C-N bond under the catalysis of the catalysis of a cinchona alkaloid derivative chiral tertiary amine. At room temperature, the a-methylene-β-amino esters were obtained in good yields with excellent enantioselectivities (up to 99%ee) for a wide range of MBH carbonates in 1,4-dioxane. Furthermore, the unprotected a-methylene-β-amino esters were easily obtained with retentive enantioselectivities via one-step acidic hydrolysis protocol for the first time.
Part IV:We have described the enantioselective Friedel-Crafts alkylation reaction between indoles and 2,2,2-trifluoroacetophenones under the catalysis of a chiral bifuncational catalyst derivated from cinchona alkaloid. At 5℃, the chiral trifluoromethyl substituted tertiary alcohols with a quaternary stereocenter were obtained in good yields with moderate to good enantioselectivies in DCE.
第一部分,我们以脯胺醇衍生的催化剂实现了β-酮磷酯的不对称α-硫代反应,成功地构建了手性碳-硫键。0℃条件下,正己烷溶剂中考察了一系列环状β-酮磷酯与N-苯硫基邻苯二甲酰亚胺的反应情况,以较高的产率和对映选择性(upto 92% ee)获得了具有手性季碳中心的α-硫代β-酮磷酯类化合物。通过CD光谱确定了产物的绝对构型,并且根据反应结果推测了反应活化模式为分子间氢键活化机理,而非共价键机理。
第二部分,我们以金鸡钠碱衍生的手性叔胺为催化剂,实现了MBH酯衍生物与烷基硫醇的不对称取代反应,再次成功地构建手性碳-硫键。10℃条件下,1,4-二氧六环溶剂中,以优秀的产率和极高的对映选择性(up to 97%ee)获得相应的α-亚甲基-β-硫酯类化合物。我们通过单晶衍射确定了产物的绝对构型,简单的操作和广泛的底物范围使得该反应具有很强的实用前景。
第三部分,我们再次以金鸡钠碱衍生的手性叔胺为催化剂,实现了MBH酯衍生物与二苯甲酮亚胺的不对称胺化反应,成功构建手性碳-氮键。室温条件下,1,4-二氧六环溶剂中,以较高的产率和极高的对映选择性获得相应的α-亚甲基-β-胺基酯类化合物。随后我们经过一步酸化水解过程,首次高效地获得了未保护的a-亚甲基-β-胺基酯。
第四部分,我们以金鸡钠碱衍生的双官能手性胺实现了吲哚和2,2,2-三氟苯乙酮的不对称F-C烷基化反应。5℃条件下,1,2-二氯乙烷溶剂中以较好的产率和中等的对映选择性获得具有手性季碳中心和三氟甲基取代的叔醇类化合物。
In recent years, asymmetric organocatalysis is a rapidly growing field and now has been as the third general approach to the catalytic production of enantiomerically pure organic compounds between the extremes of enzymatic transformations and transition metal catalysis. Moreover, the construction of chiral carbon-heteroatom bond, either of the foundation of the research methodology, or the synthesis of important drug molecules and natural products, is of practical significance and application value, also this will be a long-term attention and research hot spot for organic chemist. This dissertation mainly focuses on the design and research of asymmetric organocatalytic carbon-heteroatom bond formation reaction, which is divided into four parts.
Part I:We have successfully developed the enantioselective sulfenylation ofβ-keto phosphonates and constructed the chiral C-S bond under the catalysis ofα,α-diaryl-L-prolinols. At 0℃, theα-sulfenylatedβ-keto phosphonates with a quaternary stereocenter were obtained in good yields and with excellent enantioselectivities (up to 92%ee) for variousβ-keto phosphonates and N-(arylthio)-phthalimides in hexane. The absolute configuration of the product was determined to be R by means of comparison of the CD spectrum. And on the basis of the results, the activation mode of the reaction may be attributed to a molecular interaction rather than a covalent bond.
PartⅡ:We have provided a highly efficient organocatalytic enantioselective C-S bond formation reaction between simple alkyl thiols and Morita-Baylis-Hillman (MBH) carbonates under the catalysis of a cinchona alkaloid derivative chiral tertiary amine. At 10℃, the optically activeα-methyleneβ-mercapto esters could be obtained in good yields with excellent enantioselectivities (up to 97%ee) for a wide range of alkyl thiols and MBH carbonates in 1,4-dioxane. And the absolute configuration of the product was determined to be S by means of an X-ray crystallographic analysis, the broad scope and simple operation makes this methodology very practical.
Part III:We have provided a highly efficient asymmetric amination reaction of Morita-Baylis-Hillman (MBH) carbonates with benzophenone imine and constructed the chiral C-N bond under the catalysis of the catalysis of a cinchona alkaloid derivative chiral tertiary amine. At room temperature, the a-methylene-β-amino esters were obtained in good yields with excellent enantioselectivities (up to 99%ee) for a wide range of MBH carbonates in 1,4-dioxane. Furthermore, the unprotected a-methylene-β-amino esters were easily obtained with retentive enantioselectivities via one-step acidic hydrolysis protocol for the first time.
Part IV:We have described the enantioselective Friedel-Crafts alkylation reaction between indoles and 2,2,2-trifluoroacetophenones under the catalysis of a chiral bifuncational catalyst derivated from cinchona alkaloid. At 5℃, the chiral trifluoromethyl substituted tertiary alcohols with a quaternary stereocenter were obtained in good yields with moderate to good enantioselectivies in DCE.
引文
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