What question did this study set out to answer?

To explore the use of multifunctional organocatalysts in the asymmetric Mannich reaction of aromatic imines and malonates.

January 18, 2026Open Access

Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts

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Key Points

To explore the use of multifunctional organocatalysts in the asymmetric Mannich reaction of aromatic imines and malonates.
Synthesis of various enantiomerically pure organocatalysts.
Screening of catalysts in asymmetric Mannich reactions.
Investigation of reaction conditions affecting stereoselectivity.
Achieved Mannich adducts with enantiomeric purities up to 98% ee.
Demonstrated that hydrogen and halogen bonds enhance reaction selectivity.
Highlighted the role of steric effects from the tert-butyl group in the catalysts.

Abstract

Various multifunctional enantiomerically pure organocatalysts were synthesized and screened in asymmetric Mannich reaction. The reaction of aromatic imines with malonates in the presence of amino acid-derived catalysts gave Mannich adducts in very high enantiomeric purities (up to 98% ee). It is proposed that a network of hydrogen and halogen bonds with Lewis bases, together with the steric effect of the tert -butyl group of the catalyst, is responsible for the high stereoselectivity of the reaction.

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Authors

Kadri Kriis

Harry Martõnov

Annette Miller

Journals

Beilstein Journal of Organic Chemistry

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Asymmetric Mannich reaction of aromatic imines with malonates in the presence of multifunctional catalysts

Key Points

Abstract

Citation Network

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Discussion

Authors

Journals

Actions

References and Citations

Citation Network

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Discussion

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