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Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes. / Weiqiang Zhang

Swansea University Author: Weiqiang Zhang

Abstract

The thesis reports the total syntheses of new chiral pyrrolidine-type salen ligands 5.4 and their corresponding Mn(III) complexes 5.5. The salen ligands were synthesized by condensation of tras-(3R,4R)-diaminopyrrolidine (3.12) or trans-(3R,4R)-1-benzyl-3,4-diaminopyrrolidine (3.10) with two equival...

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Published: 2006
Institution: Swansea University
Degree level: Doctoral
Degree name: Ph.D
URI: https://cronfa.swan.ac.uk/Record/cronfa42403
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spelling 2018-08-02T16:24:29.1037902 v2 42403 2018-08-02 Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes. b033a9bc9d33b5094282e5046ac6959f NULL Weiqiang Zhang Weiqiang Zhang true true 2018-08-02 The thesis reports the total syntheses of new chiral pyrrolidine-type salen ligands 5.4 and their corresponding Mn(III) complexes 5.5. The salen ligands were synthesized by condensation of tras-(3R,4R)-diaminopyrrolidine (3.12) or trans-(3R,4R)-1-benzyl-3,4-diaminopyrrolidine (3.10) with two equivalents of (R)-3-formyl-2-hydroxy-2'-phenyl-1,1'-binaphthalene [(R)-4.9]. The salen ligands were transformed to their corresponding Mn(III) complexes following a general procedure. The catalytic performances of the synthesized (salen)Mn(III) complexes in asymmetric epoxidation of 1,2-dihydronaphthalene were tested. In chapter 1, a review of asymmetric epoxidation of alkenes is given. Emphasis is placed on the development and some of the important designs of chiral salen ligands and their corresponding (salen)Mn(III) complexes. In chapter 2, the nature of the research project is outlined. In chapter 3, the syntheses of trans-(3R,4R)-diaminopyrrolidine trihydrochloride salt (3.9), trans-(3R,4R)-1-benzyl-3,4-diaminopyrrolidine (3.10) and its trihydrochloride salt (3.11) are reported. These compounds were prepared from (2R,3R)-(-i-)-tartaric acid via multi-step syntheses. Extensive studies on optimization of these transformations are reported. Chapter 4 records the synthesis of (R)-3-formyl-2-hydroxy-2'-phenyl-1,1'-binaphthalene [(R)-4.9] from 2-naphthol via a seven-step synthetic procedure. Extensive studies on these transformations are described, especially on the oxidative coupling of 2-naphthol and on the optical resolution of racemic 2,2'-dihydroxy-1,1'-binaphthalene. In chapter 5, the preparations of salen ligands 5.4 and their corresponding Mn(III) complexes 5.5 are reported. The applications of synthesized Mn(III) complexes in asymmetric epoxidation of 1,2-dihydronaphthalene were carried out. In chapter 6, an overall conclusion of the work is given. E-Thesis Organic chemistry. 31 12 2006 2006-12-31 COLLEGE NANME Chemistry COLLEGE CODE Swansea University Doctoral Ph.D 2018-08-02T16:24:29.1037902 2018-08-02T16:24:29.1037902 Faculty of Science and Engineering School of Engineering and Applied Sciences - Chemistry Weiqiang Zhang NULL 1 0042403-02082018162451.pdf 10798111.pdf 2018-08-02T16:24:51.6470000 Output 6542194 application/pdf E-Thesis true 2018-08-02T16:24:51.6470000 false
title Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
spellingShingle Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
Weiqiang Zhang
title_short Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
title_full Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
title_fullStr Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
title_full_unstemmed Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
title_sort Synthesis of novel chiral pyrrolidine-type (salen)Mn(III) complexes.
author_id_str_mv b033a9bc9d33b5094282e5046ac6959f
author_id_fullname_str_mv b033a9bc9d33b5094282e5046ac6959f_***_Weiqiang Zhang
author Weiqiang Zhang
author2 Weiqiang Zhang
format E-Thesis
publishDate 2006
institution Swansea University
college_str Faculty of Science and Engineering
hierarchytype
hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Chemistry{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Chemistry
document_store_str 1
active_str 0
description The thesis reports the total syntheses of new chiral pyrrolidine-type salen ligands 5.4 and their corresponding Mn(III) complexes 5.5. The salen ligands were synthesized by condensation of tras-(3R,4R)-diaminopyrrolidine (3.12) or trans-(3R,4R)-1-benzyl-3,4-diaminopyrrolidine (3.10) with two equivalents of (R)-3-formyl-2-hydroxy-2'-phenyl-1,1'-binaphthalene [(R)-4.9]. The salen ligands were transformed to their corresponding Mn(III) complexes following a general procedure. The catalytic performances of the synthesized (salen)Mn(III) complexes in asymmetric epoxidation of 1,2-dihydronaphthalene were tested. In chapter 1, a review of asymmetric epoxidation of alkenes is given. Emphasis is placed on the development and some of the important designs of chiral salen ligands and their corresponding (salen)Mn(III) complexes. In chapter 2, the nature of the research project is outlined. In chapter 3, the syntheses of trans-(3R,4R)-diaminopyrrolidine trihydrochloride salt (3.9), trans-(3R,4R)-1-benzyl-3,4-diaminopyrrolidine (3.10) and its trihydrochloride salt (3.11) are reported. These compounds were prepared from (2R,3R)-(-i-)-tartaric acid via multi-step syntheses. Extensive studies on optimization of these transformations are reported. Chapter 4 records the synthesis of (R)-3-formyl-2-hydroxy-2'-phenyl-1,1'-binaphthalene [(R)-4.9] from 2-naphthol via a seven-step synthetic procedure. Extensive studies on these transformations are described, especially on the oxidative coupling of 2-naphthol and on the optical resolution of racemic 2,2'-dihydroxy-1,1'-binaphthalene. In chapter 5, the preparations of salen ligands 5.4 and their corresponding Mn(III) complexes 5.5 are reported. The applications of synthesized Mn(III) complexes in asymmetric epoxidation of 1,2-dihydronaphthalene were carried out. In chapter 6, an overall conclusion of the work is given.
published_date 2006-12-31T03:52:54Z
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score 11.036334

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