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Synthesis and resolution of novel chiral pyridylphenols and their applications in catalytic asymmetric addition of diethylzinc to aldehydes.

by Huichang Zhang. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1996. / Includes bibliographical references (leaves 114-130). / Acknowledgment --- p.i / Abstract --- p.ii / Abbreviations --- p.iii / Table of Contents --- p.iv-v / Chapter Chapter I --- Introduction --- p.1 / Chapter I --- The basis of asymmetric catalysis --- p.6 / Chapter II --- Chiral catalyst --- p.8 / Chapter II-I --- Center metal --- p.9 / Chapter II-II --- Chiral ligand --- p.10 / Chapter III --- Structural analysis of effective chiral ligands --- p.13 / Chapter III-I --- Monodentate ligand --- p.15 / Chapter III-II --- Bidentate Ligand --- p.16 / Chapter 1 --- Bidentate phosphine ligand --- p.16 / Chapter 2 --- Bidentate oxygen ligand --- p.17 / Chapter 3 --- Bidentate nitrogen ligand --- p.19 / Chapter 4 --- "Bidentate ligand with N, 0,P, or S donor atom" --- p.21 / Chapter III-III --- Potentially tridentate ligand --- p.22 / Chapter III-IV --- Potentially tetradentate ligand --- p.23 / Chapter IV --- Tentative conclusions on the effect of structural elements --- p.24 / Chapter Chapter II --- "Design, synthesis and resolution of novel chiral pyridylphenols" --- p.27 / Chapter I --- Design of chiral ligand --- p.27 / Chapter II --- Synthesis of chiral ligands --- p.29 / Chapter II-I --- "Synthesis of the chiral N, O-donor ligands" --- p.29 / Chapter 1 --- Synthesis of the chiral ligands 75a-75c --- p.29 / Chapter 2 --- Synthesis of the chiral ligands 93a and 93b --- p.37 / Chapter 3 --- Synthesis of the chiral ligands 97a-97c --- p.41 / Chapter II-II --- "Synthesis of the chiral N, P-donor ligand 98 and N, S-donor ligand 101" --- p.42 / Chapter III --- Resolution of racemates of chiral ligands --- p.44 / Chapter III-I --- Resolution of of the pyridylphenol 75b --- p.44 / Chapter III-II --- Resolution of of the pyridylphenol 93a --- p.48 / Chapter III-III --- Racemization study of 75b and 93a --- p.52 / Chapter 1 --- Racemization test of 75b --- p.52 / Chapter 2 --- Racemization test of 93a --- p.52 / Chapter Chapter III --- Asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by chiral pyridylphenols / Chapter I --- Backgound --- p.53 / Chapter II --- Asmmetric addition of Et2Zn to aldehydes catalyzed by chiral pyridylphenols --- p.61 / Chapter II-I --- Asmmetric addition of Et2Zn to aldehydes catalyzed by (R)-(+)-75b --- p.61 / Chapter 1 --- The influence of the solvent --- p.61 / Chapter 2 --- The influence of the reaction temperature --- p.64 / Chapter 3 --- The influence of the concentration of catalyst --- p.66 / Chapter 4 --- Electronic effect on the enantioselectivity of asymmetric addition of Et2Zn to aromatic aldehydes --- p.67 / Chapter II-II --- Asmmetric addition of Et2Zn to aldehydes catalyzed by (5)-(+)-75b --- p.73 / Chapter II-III --- Asmmetric addition of Et2Zn to aldehydes catalyzed by (R)-(+)-93a --- p.75 / Chapter III --- Conclusions --- p.78 / Chapter Chapter V --- Experimental Section --- p.79 / References --- p.114 / NMR Spectra --- p.131

Identiferoai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_322585
Date January 1996
ContributorsZhang, Huichang., Chinese University of Hong Kong Graduate School. Division of Chemistry.
Source SetsThe Chinese University of Hong Kong
LanguageEnglish
Detected LanguageEnglish
TypeText, bibliography
Formatprint, v, 186 leaves : ill. ; 30 cm.
RightsUse of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/)

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