Development and Application of Quinone-Catalyzed C-C Bond Cleavage

Abstract

Organocatalysis is a synthetic field of ever increasing development and utility. Of the reactions and small molecule catalysts developed over the last 20 years, a considerable portion have been inspired by cofactors that are important to biological systems. Research in the Clift group focuses on developing modes for catalysis through applications of quinone cofactor mimics. Our studies were motivated by developing a new synthesis of β-amino acids through quinone-catalyzed oxidative-decarboxylation. In this process, we developed a protocol for quinone-catalyzed oxidative-decarboxylation of α-aryl amino acids in which homologation products were isolated following Mukaiyama−Mannich addition. In all, isolated 20 homologated products (15-95% yields) in first demonstration of quinone-catalyzed oxidative-decarboxylation of α-aryl amino acids. Following the development of quinone-catalyzed oxidative-decarboxylation, we sought to explore the potential of quinone catalysts in related oxidative C–C bond cleavage reactions. Initial studies on the development of a protocol for the deformylation of amino alcohols is shown as well.