Synthesis And Chiral Resolution Of Aminophenols As Well As Their Applications In Asymmetric Synthesis

Chiral amino-hydroxy compounds have been proved to be a very efficient class of ligands in a variety of catalytic asymmetric syntheses and chiral auxiliary synthesis catalyzed by metallic ions. Most of them were derived from a few readily available natural products. To increase understanding of asymmetric synthesis, design and synthesis of chiral ligands from non-natural resource is essential. Therefore, chiral amino-phenol compounds are gaining progressive importance.The thesis here described the chiral resolution of Betti Base and the synthesis of their derivatives, as well as their applications as chiral ligands in asymmetric synthesis.In the Chapter One, we found the reason that led the decomposition of Betti Base 1 in the process of chiral resolution and an efficient resolution procedure was developed using acetone as the solvent. In the scale of 50 grams, it gave the resolution results in up to 84% yield and 99%ee.In the Chapter Two, bis-nuclear coordination compounds were prepared by the reaction of compound 5-1, 2-hydroxybenzaldehyde and Cu(OAc)2. Their structures were confirmed by X-ray diffraction analysis and the catalytic properties were tested in the asymmtric cyclopropanation.The TV-substituted 5-1 were also synthesized and the catalytic properties were tested in the asymmtric reduction of 2'-bromoacetophenone.