Research

Chemical Sciences

Title :

Development of Sugar Derived Bi-PHENOL-Phosphate Brønsted Acid Organocatalysts and its Metal Catalysts for Asymmetric Synthesis.

Area of research :

Chemical Sciences

Principal Investigator :

Dr. Seenuvasan Vedachalam, National Institute Of Technology (NIT) Puducherry

Timeline Start Year :

2022

Timeline End Year :

2024

Contact info :

Equipments :

Details

Executive Summary :

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).

Total Budget (INR):

31,37,520

Organizations involved