2. Catalytic a-Functionalization of Common Organic Building Blocks

 

A part of our research is devoted to develop a-functionalization strategies for common organic substrates, for example carboxylic acids, amides, esters, ketones etc. These functionalizations are primarily targeted to achieve or functionalize significant bioactive compounds.

In general, the a-functionalization of carboxylic acid derivatives requires either a transition metal catalyst or stoichiometric activating agent/strong base/external additive. We have developed a transition metal-free a-chalcogenation of aliphatic carboxylic acid equivalents via ion pair formation using K3PO4 as a catalyst. The synthetic methodology has many merits including mild condition, broad scope, scalability of the process etc. It was eventually applied to attain bioactive Shingosine-1-Phosphate antagonist/agonist, glucokinase activators and some synthetic intermediates.

 

 

 

 

 

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Development of catalytic direct a-functionalization approaches for ketones (and/or carbonyl compounds) is an important class of synthetic transformation to access a broad range of functionalized ketones of choice. In this context, our group is actively involved in unveiling practical a-functionalization strategies of ketones. Thus far, we have reported elegant methods toward a-cyanomethylenation, a-allylic alkylation etc. of ketones under palladium catalysis.