An organocatalytic asymmetric Mannich reaction for the synthesis of 3,3-disubstituted-3,4-dihydro-2-quinolones

Organic & Biomolecular Chemistry
Soumendranath Mukhopadhyay, Subhas Chandra Pan

Abstract

The first organocatalytic asymmetric Mannich reaction employing 3,4-dihydro-2-quinolones has been developed for the synthesis of biologically important 3,3-disubstituted-dihydro-2-quinolones. N-Boc imine precursor amidosulfones as well as pre-formed N-Boc imine were used for this purpose. Cyclohexyldiamine derived bifunctional amino-thiourea catalysts were employed to provide the products in high enantio- and good diastereoselectivities.

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Methods Mentioned

BETA
silica
gel column chromatography
X-ray

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