基于Binol和氨基酸的Salen-锰（Ⅲ）手性配合物的合成、表征以及催化性质的研究
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摘要
近年来希夫碱金属配合物在催化不对称合成方面的应用受到人们的广泛关注,特别是具有高反应活性,高对映体选择的催化非官能团化烯烃环氧化手性Salen-Mn(III)催化体系。探讨催化剂结构,反应条件,催化剂回收和循环使用等因素,进一步深化和发展Salen-Mn(III)催化体系。本论文主要从锰(Ⅲ)-Binol-Salen配合物的设计与合成、空间位阻、反应条件、手性中心协同作用及催化剂的循环利用等几方面进行了重点研究。考察这些配合物对非官能团化烯烃环氧化反应的催化效果,为催化不对称反应的发展提供有用的信息。
本论文共分为五章：
第一章：介绍各类不对称催化环氧化体系的最新研究现状,简要综述各类催化体系的特点,并对论文的选题目的及意义做了概述。
第二章：将手性Binol引入希夫碱配体中,成功的合成了四个具有对称结构的Binol-Salen配体H2L1-4及相应的锰(Ⅲ)配合物,研究了配合物的结构变化对配合物催化稀烃环氧化性质的影响。实验结果表明催化剂具有良好的催化性质,尤其是以配体H2L3所合成的催化剂。
本章涉及到的配体是：N,N′-双((s)-1,1′-2-羟基-2′-异丙氧基-3-亚萘基)-1,2-乙二胺(H2L1)N,N′-双((S)-1,1′-2-羟基-2′-异丙氧基-3-亚萘基)-1,2-丙二胺(H2L2)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2’-异丙氧基-3-亚萘基)-1,2-环乙二胺(H2L3)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2′-异丙氧基-3-业萘基)-1,2-二苯基乙二胺(H2L4)
第三章：使用不同取代基的半边胺和手性3-甲酰-2-羟基-2′-甲氧基-1,1’-联萘成功的合成了四个具有不同手性中心和取代基的不对称Binol-Salen配体H2L5-8及其锰(Ⅲ)配合物。为进一步研究催化的对称性对催化效果的(?)了对称的Binol-Salen配体H2L9及其锰(Ⅲ)配合物。考察了这五个配合(?)烃催化环氧化的对映体选择情况。实验结果表明这五个B(?)(?)合物催化烯烃具有高效特点,取得了优良的对映体选择.
本章涉及到的配体是：(S)-3-((E)-((1R,2R)-2-((E)-2-羟基苯亚基胺)环己亚胺)甲基)-2’-甲氧基-1,1’-联萘-2-酚(H2L5)(S)-3-((E)-((1R,2R)-2-((E)3-叔丁基-2-羟基苯亚基胺)环己亚胺)甲基)甲氧基-1,1’-联萘-2-酚(H2L6)(S)-3-((E)-((1R,2R)-2-((E)3,5-二-叔丁基-2-羟基苯亚基胺)环己亚胺)基)-2’-甲氧基-1,l’-联萘-2-酚(H2L7)(S)-3-((E)-((1R,2R)-2-((E)3,5-二-叔丁基-2-羟基苯亚基胺)苯亚胺)甲基)-2’-甲氧基-1,1’-联萘-2-酚(H2L8)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2′-甲氧基-3-亚萘基)-1,2-环乙.胺(H2L9)
第四章：Salen-Mn(Ⅲ)配合物的水溶性和催化剂的简单回收和循环使用是现在研究Salen配合物对烯烃催化环氧化的热点。低聚多核催化剂在催化烯烃时能够实现催化剂的回收和循环使用。合成了三个具有对称结构多手性中心的Binol-Salen配体H4L10-12及其锰(Ⅲ)配合物。为了探讨配合物的水溶性我们还合成了具有相转移能力的对称结构的Salen配体H4L13-14及其锰(Ⅲ)配合物。实验结果表明五个低聚多核锰(Ⅲ)配合物催化烯烃实现了催化剂与产物的简单分离和催化剂的多次催化循环使用。研究了这些配合物在不同的反应条件下对烯烃催化性质,这为寻找高效可循环使用的催化剂提供了一些有用信息。
本章涉及到的配体是：(S)-3,3’-双((E)-((1R,2R)-2-((E)-3-叔丁基-2-羟基苯二胺)-1,2-二苯基乙亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L10)(S)-3,3’-双((E)-((1R,2R)-2-((E)-3,5-二叔丁基-2-羟基苯二胺)-1,2-二苯摹乙二亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L11)(S)-3,3’-双((E)-((1R,2R)-2-((E)-3,5-二叔丁基-2-羟基苯二胺)-环己二胺亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L12)5,5-业甲基双-[(R,R)-{N-(3-叔丁基水杨醛)-N’-(3’-叔丁基-5’-(N,N-二正丁基业甲基)水杨醛)}-1,2-二苯基乙二胺](H4L13)5,5-业甲基双-[(R,R)-{N-(3-叔丁基水杨醛)-N’-(3’-叔丁基-5’-(N,N-二正丁基亚甲基)水杨醛)}-1,2-环乙二胺](H4L14)
第五章：使用不同取代基的氨基酸和3,5-二-叔丁基水杨醛成功的合成了四个不对称的类Salen配体H2L15-18及其锰(Ⅲ)配合物。考察了这四个配合物对烯烃催化环氧化的对映体选择情况。实验结果表明这四个类Salen配体的锰(Ⅲ)配合物催化烯烃具有高效特点,取得了优良的对映体选择。
本章涉及到的配体是：(E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)乙酰胺(H2L15)((R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)丙酰胺(H2L16)(R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)-3-甲基丁酰胺(H2L17)(R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)-3-苯基丙酰胺(H2L18)
Schiff-base complexes have attracted explosive interest in recent years due to their wide application in the field of catalytic asymmetric synthesis. In particular, the Salen-Mn(III) catalytic system had emerged as a highly reactive and a highly enantioselective system for the asymmetric epoxidation of non-functionalized alkenes. In order to improve the catalytic application of Salen-Mn(III) system, many attempts have been made to investigate the influence factors in the asymmetric catalysis (e.g., the catalyst structure, reaction condition, recovery and reuse of catalyst, and so on). The paper is focused on the design and synthesis of Mn(III)-Binol-Salen complexes and the investigation of steric factors, reaction condition, cooperation of chiral center, and recovery and reuse of catalyst.The catalytic properties of these complexes on unfunctionalized alkene have been tested and employed in the asymmetric epoxidation. they provided some useful information for the development of catalytic asymmetric synthesis.
This paper consists of five chapters
1. It was given a brief rewiew of the research progress about the studies in the catalytic asymmetric epoxidation and the character of different asymmetric catalytic system. Further more, the aim and significance of this thesis have been outlined.
2. Herein, four novel chiral C2-symmetric Binol-Salen ligands H2L1-4 derived from chiral Binol as well as the corresponding Manganese(III) complexes have been designed and further synthesized, the influence of the different ligands to the catalytic properties of complexes have been investigated. The positive experimental results have proved that those complexes effective catalysts for the asymmetric epoxidation of alkenes. especially the catalyst derived from H2L
Four ligands were involved in this chapter:
N, N'-Bis ((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-ethylenediamine (H2L1)
N. N'-Bis ((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-propanediamine (H2L2)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-cyclohexanediamine (H2L3)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-diphenylethylenediamine (H2L4)
3. Four novel chiral unsymmetrical Binol-Salen ligands H2L5-8 derived from chiral 3-Formyl-2-hydroxy-2'-methoxy-1,1'-binaphthyl and half-unit amine with different substituted groups as well as the corresponding Manganese(III) complexes have been designed and synthesized. In order to further researth the influence of catalytic properties, one C2-symmetric Binol-Salen ligand H2L9 and corresponding Manganese(III) complexes have also been synthesized. The catalytic properties of complexes have been investigated. Experimental results have proved that the five complexes effective catalysts for the asymmetric epoxidation of alkenes. Five ligands were involved in this chapter:
(S)-3-((E)-((1R,2R)-2-((E)-2-hydroxybenzylideneamino)cyclohexylimino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L5)
(S)-3-((E)-((1R,2R)-2-((E)-3-tert-butyl-2-hydroxybenzylideneamino)cyclohexylimino )methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L6)
(S)-3-((E)-((1R,2R)-2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)cyclohexyli mino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L7)
(S)-3-((E)-(2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)phenylimino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol(H2L8)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-methoxy-3-naphthylidene)-1,2-diphenylethylenediamine (H2L9)
4. Particular interest has been focused on the recovery capability for reuse and water-solubility of Salen-Mn(Ⅲ) complexes in the asymmetric epoxidation. The oligomeric catalyst could be recovered and recycled for the asymmetric epoxidation of non-functionalized alkenes. Based on these facts, three novel chiral symmetrical Binol-Salen ligands H4L10-12 with many different chiral center as well as the corresponding Manganese(Ⅲ) complexes have been designed and synthesized. To further researth the water-solubility of catalyst, two C2-symmetric Salen ligand H4L13-14 with inherent phase-transfer capability and corresponding Manganese(III) complexes have also been synthesized. The catalytic properties of complexes have been investigated under different reaction condition. Experimental results have proved that those five catalysts can recovered and recycled for server times without losing activity and selectivity. The positive experimental results provided some useful information for the development of highly active catalyst with recovery capability.
Five ligands were involved in this chapter:
(S)-3,3'-bis((E)-((1R,2R)-2-((E)-3-tert-butyl-2-hydroxybenzylideneamino)-1,2-diphen ylethylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L10)
(S)-3,3'-bis((E)-((1R,2R)-2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)-1,2-di phenylethylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L11)
(S)-3,3'-bis((E)-((1S,2S)-2-((E)-3.5-di-tert-butyl-2-hydroxybenzylideneamino)cyclohe xylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L12)
5,5-methylenedi-[(R,R)-{N-(3-tert-butylsalicylidine)-N'-(3'-tert-butyl-5'-(N,N-dibutylmethylene)salicyladhyde)}-1,2-diphenylethylenedi amine] 1(H4L13)
5.5-methylenedi-[(R,R)-{N-(3-tert-butylsalicylidine)-N'-(3'-tert-butyl-5'-(N.N-dibuty lmethylene)salicyladhyde)}-1,2-cyclohexanediamine] 1(H4L14)
5. Four novel chiral unsymmetrical Salen-like ligands H2L15-18 derived from amino acids and 3,5-Di-tert-butylsalicylaldehyde as well as the corresponding Manganese(Ⅲ) complexes have been designed and further synthesized, the influence of the different ligands to the catalytic properties of complexes have been investigated. The positive experimental results have proved that those complexes effective catalysts for the asymmetric epoxidation of alkenes.
Four ligands were involved in this chapter: (E)-2-(3.5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)acetamide (H2L15)
(R.E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)propana mide (H2L16)
(R,E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)-3-meth ylbutanamide (H2L17)
(R,E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)-3-phen ylpropanamide (H2L18)
本论文共分为五章：
第一章：介绍各类不对称催化环氧化体系的最新研究现状,简要综述各类催化体系的特点,并对论文的选题目的及意义做了概述。
第二章：将手性Binol引入希夫碱配体中,成功的合成了四个具有对称结构的Binol-Salen配体H2L1-4及相应的锰(Ⅲ)配合物,研究了配合物的结构变化对配合物催化稀烃环氧化性质的影响。实验结果表明催化剂具有良好的催化性质,尤其是以配体H2L3所合成的催化剂。
本章涉及到的配体是：N,N′-双((s)-1,1′-2-羟基-2′-异丙氧基-3-亚萘基)-1,2-乙二胺(H2L1)N,N′-双((S)-1,1′-2-羟基-2′-异丙氧基-3-亚萘基)-1,2-丙二胺(H2L2)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2’-异丙氧基-3-亚萘基)-1,2-环乙二胺(H2L3)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2′-异丙氧基-3-业萘基)-1,2-二苯基乙二胺(H2L4)
第三章：使用不同取代基的半边胺和手性3-甲酰-2-羟基-2′-甲氧基-1,1’-联萘成功的合成了四个具有不同手性中心和取代基的不对称Binol-Salen配体H2L5-8及其锰(Ⅲ)配合物。为进一步研究催化的对称性对催化效果的(?)了对称的Binol-Salen配体H2L9及其锰(Ⅲ)配合物。考察了这五个配合(?)烃催化环氧化的对映体选择情况。实验结果表明这五个B(?)(?)合物催化烯烃具有高效特点,取得了优良的对映体选择.
本章涉及到的配体是：(S)-3-((E)-((1R,2R)-2-((E)-2-羟基苯亚基胺)环己亚胺)甲基)-2’-甲氧基-1,1’-联萘-2-酚(H2L5)(S)-3-((E)-((1R,2R)-2-((E)3-叔丁基-2-羟基苯亚基胺)环己亚胺)甲基)甲氧基-1,1’-联萘-2-酚(H2L6)(S)-3-((E)-((1R,2R)-2-((E)3,5-二-叔丁基-2-羟基苯亚基胺)环己亚胺)基)-2’-甲氧基-1,l’-联萘-2-酚(H2L7)(S)-3-((E)-((1R,2R)-2-((E)3,5-二-叔丁基-2-羟基苯亚基胺)苯亚胺)甲基)-2’-甲氧基-1,1’-联萘-2-酚(H2L8)(1R,2R)-(-)-N,N′-双((S)-1,1′-2-羟基-2′-甲氧基-3-亚萘基)-1,2-环乙.胺(H2L9)
第四章：Salen-Mn(Ⅲ)配合物的水溶性和催化剂的简单回收和循环使用是现在研究Salen配合物对烯烃催化环氧化的热点。低聚多核催化剂在催化烯烃时能够实现催化剂的回收和循环使用。合成了三个具有对称结构多手性中心的Binol-Salen配体H4L10-12及其锰(Ⅲ)配合物。为了探讨配合物的水溶性我们还合成了具有相转移能力的对称结构的Salen配体H4L13-14及其锰(Ⅲ)配合物。实验结果表明五个低聚多核锰(Ⅲ)配合物催化烯烃实现了催化剂与产物的简单分离和催化剂的多次催化循环使用。研究了这些配合物在不同的反应条件下对烯烃催化性质,这为寻找高效可循环使用的催化剂提供了一些有用信息。
本章涉及到的配体是：(S)-3,3’-双((E)-((1R,2R)-2-((E)-3-叔丁基-2-羟基苯二胺)-1,2-二苯基乙亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L10)(S)-3,3’-双((E)-((1R,2R)-2-((E)-3,5-二叔丁基-2-羟基苯二胺)-1,2-二苯摹乙二亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L11)(S)-3,3’-双((E)-((1R,2R)-2-((E)-3,5-二叔丁基-2-羟基苯二胺)-环己二胺亚胺)甲基)-1,1’-双萘基-2,2’-二酚(H4L12)5,5-业甲基双-[(R,R)-{N-(3-叔丁基水杨醛)-N’-(3’-叔丁基-5’-(N,N-二正丁基业甲基)水杨醛)}-1,2-二苯基乙二胺](H4L13)5,5-业甲基双-[(R,R)-{N-(3-叔丁基水杨醛)-N’-(3’-叔丁基-5’-(N,N-二正丁基亚甲基)水杨醛)}-1,2-环乙二胺](H4L14)
第五章：使用不同取代基的氨基酸和3,5-二-叔丁基水杨醛成功的合成了四个不对称的类Salen配体H2L15-18及其锰(Ⅲ)配合物。考察了这四个配合物对烯烃催化环氧化的对映体选择情况。实验结果表明这四个类Salen配体的锰(Ⅲ)配合物催化烯烃具有高效特点,取得了优良的对映体选择。
本章涉及到的配体是：(E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)乙酰胺(H2L15)((R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)丙酰胺(H2L16)(R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)-3-甲基丁酰胺(H2L17)(R,E)-2-(3,5-二-叔丁基-2-羟基苯业甲基胺)-N-(2-羟基苯)-3-苯基丙酰胺(H2L18)
Schiff-base complexes have attracted explosive interest in recent years due to their wide application in the field of catalytic asymmetric synthesis. In particular, the Salen-Mn(III) catalytic system had emerged as a highly reactive and a highly enantioselective system for the asymmetric epoxidation of non-functionalized alkenes. In order to improve the catalytic application of Salen-Mn(III) system, many attempts have been made to investigate the influence factors in the asymmetric catalysis (e.g., the catalyst structure, reaction condition, recovery and reuse of catalyst, and so on). The paper is focused on the design and synthesis of Mn(III)-Binol-Salen complexes and the investigation of steric factors, reaction condition, cooperation of chiral center, and recovery and reuse of catalyst.The catalytic properties of these complexes on unfunctionalized alkene have been tested and employed in the asymmetric epoxidation. they provided some useful information for the development of catalytic asymmetric synthesis.
This paper consists of five chapters
1. It was given a brief rewiew of the research progress about the studies in the catalytic asymmetric epoxidation and the character of different asymmetric catalytic system. Further more, the aim and significance of this thesis have been outlined.
2. Herein, four novel chiral C2-symmetric Binol-Salen ligands H2L1-4 derived from chiral Binol as well as the corresponding Manganese(III) complexes have been designed and further synthesized, the influence of the different ligands to the catalytic properties of complexes have been investigated. The positive experimental results have proved that those complexes effective catalysts for the asymmetric epoxidation of alkenes. especially the catalyst derived from H2L
Four ligands were involved in this chapter:
N, N'-Bis ((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-ethylenediamine (H2L1)
N. N'-Bis ((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-propanediamine (H2L2)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-cyclohexanediamine (H2L3)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-isopropoxy-3-naphthylidene)-1,2-diphenylethylenediamine (H2L4)
3. Four novel chiral unsymmetrical Binol-Salen ligands H2L5-8 derived from chiral 3-Formyl-2-hydroxy-2'-methoxy-1,1'-binaphthyl and half-unit amine with different substituted groups as well as the corresponding Manganese(III) complexes have been designed and synthesized. In order to further researth the influence of catalytic properties, one C2-symmetric Binol-Salen ligand H2L9 and corresponding Manganese(III) complexes have also been synthesized. The catalytic properties of complexes have been investigated. Experimental results have proved that the five complexes effective catalysts for the asymmetric epoxidation of alkenes. Five ligands were involved in this chapter:
(S)-3-((E)-((1R,2R)-2-((E)-2-hydroxybenzylideneamino)cyclohexylimino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L5)
(S)-3-((E)-((1R,2R)-2-((E)-3-tert-butyl-2-hydroxybenzylideneamino)cyclohexylimino )methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L6)
(S)-3-((E)-((1R,2R)-2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)cyclohexyli mino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol (H2L7)
(S)-3-((E)-(2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)phenylimino)methyl)-2'-methoxy-1,1'-binaphthyl-2-ol(H2L8)
(1R,2R)-(-)-N,N'-Bis((S)-1,1'-2-hydroxy-2'-methoxy-3-naphthylidene)-1,2-diphenylethylenediamine (H2L9)
4. Particular interest has been focused on the recovery capability for reuse and water-solubility of Salen-Mn(Ⅲ) complexes in the asymmetric epoxidation. The oligomeric catalyst could be recovered and recycled for the asymmetric epoxidation of non-functionalized alkenes. Based on these facts, three novel chiral symmetrical Binol-Salen ligands H4L10-12 with many different chiral center as well as the corresponding Manganese(Ⅲ) complexes have been designed and synthesized. To further researth the water-solubility of catalyst, two C2-symmetric Salen ligand H4L13-14 with inherent phase-transfer capability and corresponding Manganese(III) complexes have also been synthesized. The catalytic properties of complexes have been investigated under different reaction condition. Experimental results have proved that those five catalysts can recovered and recycled for server times without losing activity and selectivity. The positive experimental results provided some useful information for the development of highly active catalyst with recovery capability.
Five ligands were involved in this chapter:
(S)-3,3'-bis((E)-((1R,2R)-2-((E)-3-tert-butyl-2-hydroxybenzylideneamino)-1,2-diphen ylethylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L10)
(S)-3,3'-bis((E)-((1R,2R)-2-((E)-3,5-di-tert-butyl-2-hydroxybenzylideneamino)-1,2-di phenylethylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L11)
(S)-3,3'-bis((E)-((1S,2S)-2-((E)-3.5-di-tert-butyl-2-hydroxybenzylideneamino)cyclohe xylimino)methyl)-1,1'-binaphthyl-2,2'-diol(H4L12)
5,5-methylenedi-[(R,R)-{N-(3-tert-butylsalicylidine)-N'-(3'-tert-butyl-5'-(N,N-dibutylmethylene)salicyladhyde)}-1,2-diphenylethylenedi amine] 1(H4L13)
5.5-methylenedi-[(R,R)-{N-(3-tert-butylsalicylidine)-N'-(3'-tert-butyl-5'-(N.N-dibuty lmethylene)salicyladhyde)}-1,2-cyclohexanediamine] 1(H4L14)
5. Four novel chiral unsymmetrical Salen-like ligands H2L15-18 derived from amino acids and 3,5-Di-tert-butylsalicylaldehyde as well as the corresponding Manganese(Ⅲ) complexes have been designed and further synthesized, the influence of the different ligands to the catalytic properties of complexes have been investigated. The positive experimental results have proved that those complexes effective catalysts for the asymmetric epoxidation of alkenes.
Four ligands were involved in this chapter: (E)-2-(3.5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)acetamide (H2L15)
(R.E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)propana mide (H2L16)
(R,E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)-3-meth ylbutanamide (H2L17)
(R,E)-2-(3,5-di-tert-butyl-2-hydroxybenzylideneamino)-N-(2-hydroxyphenyl)-3-phen ylpropanamide (H2L18)
引文
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