菲衍生物的合成及在不对称催化中的应用
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摘要
不对称催化研究中,手性配体(催化剂)的合成是非常重要的部分。为此,本文研究了一些具有9,10-二氢菲母核或者9,9'-联菲结构的手性分子的合成,并对他们在不对称催化中的应用作了初步评测。此外,也研究了氨基酸衍生的新型有机催化剂的合成及其在不对称催化中的应用。
主要内容可分为四部分:
(1)设计并且成功地实现了一种新的串联催化模型,反应中后续步骤的催化剂是前面步骤中产生的金属盐。邻位卤代的芳香醛在NiCl_2(PPh_3)_2催化下可发生串联的Ullmann/pinacol偶联反应。利用这个反应,合成了多种取代的9,10-二氢-9,10-二羟基菲,这些反式邻二醇拆分后都可能作为新的手性催化剂骨架。此外,还实现了由邻位卤代的芳香醛到9-菲酚衍生物和9,10-菲醌衍生物的“一锅法”合成。
(2)成功合成了反式9,10-二氢-9,10-二氨基菲这种新的邻二胺。利用氨基酸衍生的亚胺进行偶联反应,再经过多步转化,成功得到目标邻二胺的两种对映异构体。这个方法可以作为合成其他手性邻二胺化合物的参考。将9,10-二氢-9,10-二氨基菲与水杨醛缩合得到一种新的Salen型的衍生物,并且以这种Salen型化合物作为配体催化了苯甲醛的pinacol偶联反应。
(3)对联菲化合物的合成做了大量研究。以9-溴菲为原料,经过11步反应,以22.5-26.4%的总产率得到了4种9,9'-联菲-10,10'-双噁唑啉配体。联菲双噁唑啉配体可以用于催化吲哚和硝基烯的不对称Friedel-Crafts烷基化反应,在0℃时可以达到85%ee的选择性。联菲双噁唑啉还可以用于催化其他的反应。对于联菲酚和联菲二酸的合成、拆分、修饰和改造,也作了很多研究。
(4)针对不对称Henry反应,设计了一些氨基酸衍生的双功能有机催化剂。研究过程中发现,当α-位有两个苯基取代时,氨基的亲核性和碱性都非常弱。我们已经得到了一个带有硫脲和伯胺的双官能催化剂,正将其用于催化反应。
The synthesis of chiral ligands(or catalysts) is a very important part in the research of asymmetric catalysis.This dissertation has developed some novel chiral molecules containing a 9,10-dihydrophenanthryl structure or a 9,9'-biphenanthryl structure,which were then evaluated on their applications in the asymmetric catalysis. In addition,the synthesis and applications of some novel amino acid-derived organocatalysts were also studied.
The main content of the dissertation can be divided into four parts:
(1) A novel model of tandem catalytic reaction was developed,in which the catalyst of the sequential step is a salt produced in situ in the prior step.The ortho-halogenated aromatic aldehydes could engage in the tandem Ullmann/pinacol reactions catalyzed by NiCl_2(PPh_3)_2.Using this tandem reaction,many compounds containing a trans-9,10-dihydroxy-9,10-dihydrophenanthryl structure were synthesized.These vicinal diols would be new cores ofchiral catalysts after resolving. Moreover,'one-pot' methods to prepare the derivatives of 9-phenanthrol and 9,10-phenanthrenequinone from the ortho-halogenated aromatic aldehydes were also developed.
(2) The synthesis of trans-9,10-diamino-9,10-dihydrophenanthrene,a new vicinal diamine,was realized.The synthetic procedure employed a coupling reaction of a L-valine-derived diimine as a key step,and the two separated coupling products were converted to both the enantiomers of trans-9,10-diamino-9,10-dihydrophenanthrene each after multi-step transformations.A new Salen-type derivative was obtained by the condensation reaction of the salicalaldehyde and the enantiomeric pure vicinal diamine.This Salen-type compound was then tested as a ligand for the pinacol coupling reaction of benzaldehyde.
(3) The synthesis of 9,9'-biphenanthryl compounds were detailed studied.Four 9,9'-biphenanthryl-10,10'-bis(oxazoline)s were synthesized using the 9-bromophenan-threne as a starting material.The synthetic procedure consists of 11 steps of reactions, and the total yields ranged from 22.5%to 26.4%.The bis(oxazoline)s were employed as ligands for the Friedel-Crafts alkylations of indoles with nitroalkenes,the selectivies were up to 85%ee at 0℃.The bis(oxazoline)s could be used in other reactions.Moreover,the synthesis,resolution,modification and transformation of 9,9'-biphenanthryl-10,10'-diol and 9,9'-biphenanthryl-10,10'-dicarboxylic acid were also studied.
(4) Some novel amino acid-derived bifunctional organocatalysts were designed for the asymmetric Henry reactions.In the research,it was found that the amino group would be very weak nucleophilic and very weak alkaline if its a-carbon beared two phenyl substituents.A new organocatalyst containing a thiourea structure and a primary amino group was obtained.This bifunctional compound is now employed as a catalyst for some reactions.
主要内容可分为四部分:
(1)设计并且成功地实现了一种新的串联催化模型,反应中后续步骤的催化剂是前面步骤中产生的金属盐。邻位卤代的芳香醛在NiCl_2(PPh_3)_2催化下可发生串联的Ullmann/pinacol偶联反应。利用这个反应,合成了多种取代的9,10-二氢-9,10-二羟基菲,这些反式邻二醇拆分后都可能作为新的手性催化剂骨架。此外,还实现了由邻位卤代的芳香醛到9-菲酚衍生物和9,10-菲醌衍生物的“一锅法”合成。
(2)成功合成了反式9,10-二氢-9,10-二氨基菲这种新的邻二胺。利用氨基酸衍生的亚胺进行偶联反应,再经过多步转化,成功得到目标邻二胺的两种对映异构体。这个方法可以作为合成其他手性邻二胺化合物的参考。将9,10-二氢-9,10-二氨基菲与水杨醛缩合得到一种新的Salen型的衍生物,并且以这种Salen型化合物作为配体催化了苯甲醛的pinacol偶联反应。
(3)对联菲化合物的合成做了大量研究。以9-溴菲为原料,经过11步反应,以22.5-26.4%的总产率得到了4种9,9'-联菲-10,10'-双噁唑啉配体。联菲双噁唑啉配体可以用于催化吲哚和硝基烯的不对称Friedel-Crafts烷基化反应,在0℃时可以达到85%ee的选择性。联菲双噁唑啉还可以用于催化其他的反应。对于联菲酚和联菲二酸的合成、拆分、修饰和改造,也作了很多研究。
(4)针对不对称Henry反应,设计了一些氨基酸衍生的双功能有机催化剂。研究过程中发现,当α-位有两个苯基取代时,氨基的亲核性和碱性都非常弱。我们已经得到了一个带有硫脲和伯胺的双官能催化剂,正将其用于催化反应。
The synthesis of chiral ligands(or catalysts) is a very important part in the research of asymmetric catalysis.This dissertation has developed some novel chiral molecules containing a 9,10-dihydrophenanthryl structure or a 9,9'-biphenanthryl structure,which were then evaluated on their applications in the asymmetric catalysis. In addition,the synthesis and applications of some novel amino acid-derived organocatalysts were also studied.
The main content of the dissertation can be divided into four parts:
(1) A novel model of tandem catalytic reaction was developed,in which the catalyst of the sequential step is a salt produced in situ in the prior step.The ortho-halogenated aromatic aldehydes could engage in the tandem Ullmann/pinacol reactions catalyzed by NiCl_2(PPh_3)_2.Using this tandem reaction,many compounds containing a trans-9,10-dihydroxy-9,10-dihydrophenanthryl structure were synthesized.These vicinal diols would be new cores ofchiral catalysts after resolving. Moreover,'one-pot' methods to prepare the derivatives of 9-phenanthrol and 9,10-phenanthrenequinone from the ortho-halogenated aromatic aldehydes were also developed.
(2) The synthesis of trans-9,10-diamino-9,10-dihydrophenanthrene,a new vicinal diamine,was realized.The synthetic procedure employed a coupling reaction of a L-valine-derived diimine as a key step,and the two separated coupling products were converted to both the enantiomers of trans-9,10-diamino-9,10-dihydrophenanthrene each after multi-step transformations.A new Salen-type derivative was obtained by the condensation reaction of the salicalaldehyde and the enantiomeric pure vicinal diamine.This Salen-type compound was then tested as a ligand for the pinacol coupling reaction of benzaldehyde.
(3) The synthesis of 9,9'-biphenanthryl compounds were detailed studied.Four 9,9'-biphenanthryl-10,10'-bis(oxazoline)s were synthesized using the 9-bromophenan-threne as a starting material.The synthetic procedure consists of 11 steps of reactions, and the total yields ranged from 22.5%to 26.4%.The bis(oxazoline)s were employed as ligands for the Friedel-Crafts alkylations of indoles with nitroalkenes,the selectivies were up to 85%ee at 0℃.The bis(oxazoline)s could be used in other reactions.Moreover,the synthesis,resolution,modification and transformation of 9,9'-biphenanthryl-10,10'-diol and 9,9'-biphenanthryl-10,10'-dicarboxylic acid were also studied.
(4) Some novel amino acid-derived bifunctional organocatalysts were designed for the asymmetric Henry reactions.In the research,it was found that the amino group would be very weak nucleophilic and very weak alkaline if its a-carbon beared two phenyl substituents.A new organocatalyst containing a thiourea structure and a primary amino group was obtained.This bifunctional compound is now employed as a catalyst for some reactions.
引文
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