This research program explores new reactions of organoborn compounds and their application in short and practical preparations of bioactive substances. In addition to the studying the scope and limitations of the key reactions, this program also explores a number of synthetic strategies where the new chemistry is combined with the other powerful chemical transformation. In this manner it becomes possible to synthesize diverse multifunctional molecules rapidly and efficiently.
The specific aims of this project are: 1. New chemical reactions: a main focus of this project is the further development of the Bronco Acid Mannish reaction, a novel one-step three-component process that gives new amine or amino acid derivatives By reacting an amine with and organobornic acid or borate with certain carnal compounds. Studies are focussed on mechanistic and sterochemical aspects, and the use of functionalist organoborn derivatives. 2. New synthetic strategies: This project pursues a number of selected strategies that demonstrate the utility of the new reactions for the synthesis of various bioactive molecules. These studies combine the new chemistry with several other powerful and versatile chemical processes, including other multi component reactions, acylations, metal catalyzed coupling, olefin metathesis, and various cycloadditions. 3. Synthesis of bioactive molecules: Another goal of this synthesis of selected types of bioactive molecules that are easily accessible with the new chemistry. The targeted molecules include: pepitdomimetics, a variety of substituted heterocycles, polyol amines, aminosugars, and various molecular scaffolds as well as oligomeric systems for probing protein interactions. Overall, the chemistry in this program has a number of advantages, such as the introduction of multiple functional groups and the control of steroechemistry. It also faculties the synthesis of numerous new bioactive molecules for further studies. Therefore, this program makes new advances in organic, medicinal and combinatorial chemistry, and enhances the role of organic synthesis in biomedical research.
|Liepouri, Fotini; Bernasconi, Giovanni; Petasis, Nicos A (2015) Component-selective and stereocontrolled one-step three-component reaction among aldehydes, amines, and allenyl boronic acids or allenyl pinacolboronates. Org Lett 17:1628-31|
|Petasis, Nicos A; Butkevich, Alexey (2009) Synthesis of 2H-chromenes and 1,2-dihydroquinolines from aryl aldehydes, amines, and alkenylboron compounds. J Organomet Chem 694:1747-1753|