Dr. Pandidurai Solai

Currently working at iSm2 (Institute of Molecular Sciences of Marseille, Aix-Marseille University, France) on the synthesis of heteroatom-linked non-biaryl atropisomers via enantioselective desymmetrization strategy using chiral phosphoric acid catalyst.

I successfully developed a methodology for the synthesis of enantioenriched pyrrolo-thiazines-2-carbaldehydes and derivatives, starting from commercially available α,β-unsaturated aldehydes, and easily accessible benzothiazolium salts. The reaction, catalyzed by chiral amino organocatalysts, proceeded via 1,3-dipolar cycloaddition/rearrangement, delivering products in good yields with excellent stereocontrol (up to >99% ee, and >20:1 d.r.).

This methodology was further extended to develop an efficient enantioselective one-pot method for the synthesis of N-phenyl thioether-tethered tetrasubstituted 4,5-dihydropyrrole-3-carbaldehydes. The sequence combined 1,3-dipolar cycloaddition/rearrangement/C-S bond formation/ring-opening (C-S bond cleavage), starting from benzothiazolium salts and α,β-unsaturated aldehydes. Using (R)-diphenylprolinol trimethyl silyl ether as the catalyst, the reaction proceeded in good yields with excellent stereocontrol (>96% ee and up to >20:1 d.r.).

I developed a catalytic domino approach for the synthesis of trisubstituted 1H-pyrroles via 1,3-dipolar cycloaddition/ring-opening/C-S and C-N bond cleavage reaction sequence, starting from readily available α,β-unsaturated aldehydes and 4-metylthiazolium salts. The transformation, catalyzed by racemic diphenylprolinol trimethyl silyl ether at room temperature, afforded the desired products efficiently. This methodology was further extended to a catalytic asymmetric domino approach for the enantioselective synthesis of trisubstituted 4,5-dihydro-1H-pyrroles. The sequence involved 1,3-dipolar cycloaddition/ring-opening/C-S and C-N bond cleavage using (R)-diphenylprolinol trimethyl silyl ether as the chiral catalyst at 0 °C, affording the products in good yields and with excellent stereocontrol.

Apart from my doctoral research on enantioselective organocatalysis, I have also worked on homogeneous and heterogeneous transition metal (Pd, Pt, Cu), as well as metal nanoparticles (Pd, Pt, Cu) mediated reactions. This provided me with in-depth expertise in both organometallic chemistry and transition metal chemistry. In particular, I demonstrated the one-pot synthesis of 3-arylidene-2-oxindoles via a Heck-like carbocyclization/nucleophilic addition sequence, starting from N-(2-iodophenyl)-N-methyl-3-phenylpropiolamide, phenylacetylene, and a secondary amine, using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as a reusable catalyst.