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Updated: Apr 23, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Enantioselective Mannich reaction of β-keto esters with aromatic and aliphatic imines using a cooperatively assisted
Antti J Neuvonen1, Petri M Pihko
1Department of Chemistry and NanoScience Center, University of Jyväskylä , Survontie 9B, 40520 Jyväskylä, Finland.
Abstract:
An efficient urea-enhanced thiourea catalyst enables the enantioselective Mannich reaction between β-keto esters and N-Boc-protected imines under mild conditions and minimal catalyst loading (1-3 mol %). Aliphatic and aromatic substituents are tolerated on both reaction partners, affording the products in good enantiomeric purity. The corresponding β-amino ketones can readily be accessed via decarboxylation without loss of enantiomeric purity.
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