HCl-Catalyzed Stereoselective Mannich Reaction in H₂O-SDS System

Abstract

HCl-catalyzed Mannich reaction of cyclic ketone, aromatic aldehyde, and aromatic amine proceeded smoothly in water in the presence of SDS to afford the corresponding β-amino ketone with high anti selectivity.

Key words

Mannich reactions - Brønsted acid - water - amines - surfactant

References

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11

Although Brønsted acid-catalyzed Mannich reactions have been reported, [9] [10] high stereoselectivity has not been observed.

12

We have not observed the diaminoalkylation product.

13

Other acyclic ketones such as 2-butanone and propiophenone did not give the Mannich adduct.