Generation and virtual screening of an organocatalyst database

Organocatalysis is a relatively new, yet widely accepted field in asymmetric synthesis. Organocatalytic strategies have emerged as promising solutions in industry for sustainable development because organocatalysts have low cost, they provide high selectivity under mild reaction conditions, and they produce less waste making them environmentally friendly. The number of publications on organocatalysis has dramatically increased over the past decade. As the variety and quantity of organocatalysts increases, so does the need for a database to effectively manage this quantity of information and increase the accessibility of data. Thus, this project aims to generate a database including the physical and chemical properties of organocatalysts, their commercial availabilities, their synthetic routes, reactions they catalyzed and their three-dimensional conformational libraries and to screen this database to determine potential organocatalyst candidates for the target reactions. A total of 55 cinchona alkaloids bearing different functional groups in their structure were initially considered and their properties, availabilities in market, as well as their catalytic and synthesis reactions were recorded in the generated organocatalyst database. The database was virtually screened using catalytic atom maps obtained from quantum mechanically optimized active site models for the reactions of oxindole with nitrosobenzene and dimethyl malonate with nitrostyrene. The matching molecules were suggested as potential organocatalysts for the target reaction. The organocatalyst database and the computational screening strategy described in this thesis will enable cost effective determination of structures with high catalytic potential and easy access to all available information prior to experimental testing rather than the burdensome synthesis of numerous organocatalyst derivatives and testing of their activities.