Enantioselective Direct <i>anti</i>-Selective Mannich-type Reactions Catalyzed by 3-Pyrrolidinecarboxylic Acid in the Presence of Potassium Carbonate: Addition of Potassium Carbonate Improves Enantioselectivities
Yuvraj Garg, Fujie Tanaka
Abstract
Mannich-type reactions of cyclohexanone and related six-membered-ring ketones with N-p-methoxyphenyl-protected imines of arylaldehydes catalyzed by 3-pyrrolidinecarboxylic acid in the presence of K2CO3 that afford anti-isomers of the Mannich products with high diastereo- and enantioselectivities are reported. Addition of K2CO3 improved the enantioselectivities of the reactions catalyzed by 3-pyrrolidinecarboxylic acid while retaining the anti-selectivity of the reaction. Thus, the use of K2CO3 expands the scope of these organocatalytic reactions for providing the products with high enantioselectivities.
Topics & Concepts
ChemistryPotassium carbonateCatalysisCyclohexanonePotassiumEnantioselective synthesisOrganic chemistryMannich reactionSelectivityCarbonateAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods