Towards the Development of New Efficient Organocatalyst
Written by Gal Suez
Gal Suez and Mark Gandelman
Schulich Faculty of Chemistry, Technion- Israel Institute of Technology Haifa 32000 Israel
Over the past four decades, the dominant strategy for enantioselective catalysis has involved the utilization of metal-based catalysts. This has led to the development of numerous groundbreaking synthetic applications. Recently, organic chemists have begun to appreciate the tremendous potential offered by hydrogen bonding as a mechanism for substrate activation in small-molecule synthetic catalyst systems. Within the last few years, utilization of relatively small metal-free chiral molecules (“enzyme-like” species) which can mediate enantioselective transformations has emerged as an attractive and powerful tool in organic synthesis. Although the practical application and mechanistic understanding of these types of catalysts are in their infancy, a number of important features are already evident: (1) reactions can be performed under aerobic conditions; (2) the catalysts are inexpensive and are often more stable than enzymes or other bioorganic catalysts; (3) environmentally benign chemical processes could be expected. Here we present our efforts towards design and development of new bio-inspired class of asymmetric organocatalysts.
The design is based on the phenomenon of specific molecular recognition of DNA bases. The organocatalysts is designed to bind certain organic molecules with a complementarily pattern similar to Lewis acid-base interactions between two natural DNA bases.
Preparation, characterization and x-ray features, as well as catalytic experiments will be discussed.