Development of Sugar Derived Bi-PHENOL-Phosphate Brønsted Acid Organocatalysts and its Metal Catalysts for Asymmetric Synthesis.
Implementing Organization
Principal Investigator
Dr. Seenuvasan Vedachalam
National Institute Of Technology (NIT) Puducherry
About
In this framework, organocatalytic applications have achieved considerable attention due to selectivity, environmental friendliness, reaction course, and new synthetic plans are made possible. As typical structural features of BINOL-Phosphate, the tendency to reduce the LUMO of an electrophile through protonation and thus "activate" the substrate for the nucleophile to react. Evidently, this is an emerging topic of research, and a number of researchers are currently exploring the prospective applications of BINOL-Phosphate Brønsted acid-catalyzed creation of carbon-carbon and carbon-heteroatom bonds. In this proposal, we would like to develop sugar-based BIPHENOL-Phosphate Brønsted acid (Scheme 2) starting from 2-nitrogalactal[8a,b] and investigate to explore new asymmetric reaction using imines and new nucleophiles, ɑ-functionalized carbonyl especially -F, -Cl, -Br, -OR, -SR etc (Scheme 2 & 3). First, the sugar-based BI-PHENOL was obtained by air oxidation of the reported C-glycoside[9,10] which was further factionalized with phosphate ester group to achieve corresponding chiral phosphoric acid catalyst for the activation of various Imines to form new C-C bond formation reaction with various enolates. The chirality will be generated from the Galactose-derived substrate which could be a novel approach in terms of nature-designed catalyst. Also, we would like to explore a new approach for the synthesis of heterocycles and glycosides. Besides their role as excellent Brønsted acid catalyst, metal has replaced the proton and behave as a Lewis acid. (Figure 2). Finally, I would like to develop a new Silica support based BIPHENOL-Phosphate Brønsted acid catalyst and explorer to develop green reactions (Figure 3).