Spiro Scaffold Chiral Organocatalyst of 3,2′-Pyrrolidinyl Spirooxindole Amine and Its Catalytic Evaluation in the Enantioselective Aldol Condensation between 3-(3-Hydroxy-1H-pyrazol-1-yl)-Oxindole and Paraformaldehyde

The spiro scaffold chiral organocatalyst of 3,2'-pyrrolidinyl spiro-oxindole amine was successfully prepared from racemic spiro-oxindole amine using L-menthol as a chiral pool in 4 steps in 28%-40% overall yields with at least 99% ee in scale-up preparation, and its catalytic activity was evaluated in the enantioselective aldol condensation between 3-(3-hydroxy-1H-pyrazol-1-yl)-oxindole and paraformaldehyde. The spiro organocatalyst showed superior catalytic activity and selectivity compared with its counterparts, and most substrates offered good to excellent results with up to 96% yield in 96% ee.

Automated summary

A spiro scaffold chiral organocatalyst was prepared from racemic spiro-oxindole amine using L-menthol in 4 steps with 28%-40% overall yields, showing superior catalytic activity and selectivity in enantioselective aldol condensation. High yields and ee values up to 96% were achieved for most substrates.