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Synthesis of a Novel Water-soluble Chiral Aminophosphine Ligand and Its Application in Asymmetric Transfer Hydrogenation of Aromatic Ketones

Author: LiBaoZhu
Tutor: GaoJingXing；LiQingBiao
School: Xiamen University
Course: Chemical Engineering
Keywords: water-soluble ligand iridium complex asymmetric hydrogenation
CLC: O621.25
Type: Master's thesis
Year: 2005
Downloads: 161
Quote: 1
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Abstract


The catalytic enantioselective reduction of ketones has been extensively studied with a great success during the last decade. A particularly useful method is asymmetric transfer hydrogenation catalyzed by metal complexes associated with various chiral ligands and using iPrOH or HCOOH / Et3N as hydrogen source. Amongst these used chiral ligands, bifunctional aminophosphine ligands have emerged as very effective ligands for the enantioselective reduction reaction.However, most of these catalyst systems are sensitive to moisture so that catalytic reactions have to be performed in anhydrious solvent, and as the hydrogen source, iPrOH needs to be purified and distilled prior to use. Therefore, there is increasing interest in developing water-soluble chiral catalytic systems, which allow asymmetric transfer reaction to be carried out in water.This work will focus on the designed synthesis and characterization of new water-soluble chiral ligands, the preparation of new water-soluble chiral metal complexes, and their application in asymmetric transfer hydrogenation of aromatic ketones in water. The main results are obtained as follows:1. A novel water-soluble chiral ligand (R, R)-[C6P2(NH)2(SO3Na)4] has been synthesized by sulfonation of chiral diaminodiphosphine ligand[(R, R)-C6P2 (NH)2] with a high yield (up to 96%). This ligand reacted with Ru(DMSO)4Cl2, [RhCl(COD)]2 or IrCl(COD)(PPh3) to give a series of new water-soluble chiral metal complexes (R, R)-RuCl2C6P2(NH)2(SO3Na)4, (R, R)-RhClC6P2(NH)2 (SO3Na)4 or (R, R)-IrCl(COD)C6P2(NH)2(SO3Na)4.2. A good result for asymmetric transfer hydrogenation of acetophenone was

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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