Pyrrolidine based chiral organocatalyst for efficient asymmetric Michael addition of cyclic ketones to ß-nitrostyrenes.

An efficient asymmetric Michael addition of cyclic ketones to ß-nitrostyrenes using secondary diamine as an organocatalyst derived from l-proline and (R)-α-methylbenzyl amine has been described. This pyrrolidine based catalyst 1 was found to be very effective to synthesize various γ-nitrocarbonyl compounds in good yield (up to 81%) with excellent stereoselectivity (up to >99:1 dr and >99% ee).

Nucleophilic addition of ß-amino carbanions to arynes: one-pot synthesis of 4-aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines.

A novel approach for the direct C-4 arylation of N-methyl-1,2,3,4-tetrahydroisoquinolines by nucleophilic addition of ß-aminocarbanions to benzynes is described which provides a one-pot procedure for synthesis of the title compounds.