Stereoselective synthesis and application of pinane-based bi- and trifunctional chiral ligands

Abstract

Introduction and aims……………………………………………………………………….1 2. Literature survey………………………………………………………………………….…4 2.1.Synthesis and importance of chiral aminoalcohols……………………………………4 2.1.1. Synthesis and application of chiral alicyclic 1,3-aminoalcohols…………………4 2.1.2. Synthesis and application of chiral alicyclic 1,4-aminoalcohols…………………9 2.2. Synthesis and importance of chiral aminodiols………………………………...……14 2.2.1. Synthesis and application of chiral alicyclic 3-amino-1,2-diols…………………14 2.2.2. Synthesis and application of 2-amino-1,3-diols………………………………….192.3.Synthesis and importance of pinane-based pyrimidine compounds……………...…22 3. Results and discussion……………………………………………………………………….25 3.1. Synthesis of pinane-based chiral bi-and tri-functional ligands…………………….25 3.1.1. Synthesis of pinane-based 1,4-aminoalcohol and analogue………………………25 3.1.2. Synthesis of pinane-based 3-amino-1,2-diol and analogue……………………….30 3.1.3. Synthesis of pinane-based 2-amino-1,3-diol and analogue……………………….33 3.1.4. Application of aminodiols as chiral ligands for catalytic addition of diethylzinc to aldehyde…………………………………………………………………..39 3.1.5. Antiproliferative activity…………………………………………………………..42 3.2. Synthesis of pinane-based diaminopyrimidines………………………………….…..43 3.2.1. Synthesis of pinane-based diaminopyrimidines…………………………………..43 3.2.2. Biological properties of pinane-based diaminopyrimidines………………………46 4. Summary……………………………………………………………………………………..50