Stereoselective Synthesis of Carbocycles and Heterocycles from Vinyl Sulfoxonium Ylides
Implementing Organization
Indian Institute Of Technology Delhi
Principal Investigator
Dr. Janakiram Vaitla
Indian Institute Of Technology Delhi
vaitla@chemistry.iitd.ac.in
Project Overview
This project proposes an innovative synthetic strategy to construct stereochemically rich carbocycles and heterocycles using vinyl sulfoxonium ylides in multicomponent reactions (MCRs). Vinyl sulfoxonium ylides are versatile reagents that exhibit bifunctional (nucleophilic and electrophilic) behavior and can generate a range of reactive intermediates under appropriate conditions. Despite their promise, their use in orchestrated MCRs—particularly under metal- or photochemical catalysis—remains underexplored. Building on the team’s preliminary work, the proposal hypothesizes that these ylides can be effectively coupled with activated nucleophiles and electrophiles to achieve stereoselective and modular synthesis of complex molecular frameworks. The strategy includes the synthesis of novel stabilized sulfoxonium ylides and the development of new MCR protocols through addition, rearrangement, coupling, and photochemical pathways. Mechanistic investigations will guide the understanding of reactivity and selectivity, supported by experimental and computational studies. The proposed objectives of this project are (i) Design and synthesize a diverse set of stabilized sulfoxonium ylides with tunable electronic and steric properties. (ii) Explore their reactivity with activated coupling partners (e.g., imines, diazo compounds, electron-deficient alkenes/alkynes) under metal-catalyzed and photochemical conditions. (iii) Develop new multicomponent reaction protocols that construct stereochemically complex carbocycles and heterocycles in a modular and efficient manner. (iv) Gain mechanistic insights into the reaction pathways and intermediates using experimental and spectroscopic techniques. (v) Apply the developed methodologies to synthesize biologically relevant scaffolds of potential value in drug discovery. The proposed work represents a novel synthetic strategy that unites the distinct reactivity of vinyl sulfoxonium ylides with the metal/photochemical activated coupling partners in multicomponent reactions. By leveraging metal and photochemical activation strategies, this research aims to provide a powerful, generalizable platform for the efficient synthesis of biologically relevant scaffolds. The expected outcomes will have broad implications for drug discovery, agrochemical development, and materials science.