This dissertation consists of two sections. The common thread between these two sections is the transfer of chirality (point to helical). In the first section, (Chapters I, II and III) the absolute stereochemical determination of chiral organic molecules using the principle of chirality transfer is described. The non-covalent interaction between the receptor and chiral analyte of interest leads to induction of helicity in the host-guest complex, and the helicity is measured by circular dichroism. In Chapter I, the design and development of the bis-porphyrin based hosts that perform as "reporters of chirality" has been discussed. Chapter II describes the development of a single chiroptical sensor for the absolute stereochemical determination of α-aminophosphonates and α-hydroxyphosphonates. In chapter III, a simple chiroptical solution for the determination of absolute configuration of P(V) chiral molecules has been discussed. The developed methodology has been successfully extended to determine the absolute stereochemistry at the P center of the antiviral Sofosbuvir. In the second part of the thesis (Chapters IV), design and application of a programmable enantiodivergent organocatalyst is described. The newly developed catalyst eliminates the requirement of two enantiomeric catalysts to afford antipodal products. The asymmetry in the racemic catalyst is introduced through coordination with chiral ligands and therefore can be programmed at will. To understand the chirality transfer phenomenon (point-to-axial to point) in depth, the sterics and electronics of the catalyst and the ligands are also explored.
Read
