Highly Diastereo‐ and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts

2011/12/15 by Taichi Kano, Sunhwa Song, Yasushi Kubota +1 · 6 citations
Chemistry · #Asymmetric Synthesis and Catalysis #Carbohydrate Chemistry and Synthesis #Axial and Atropisomeric Chirality Synthesis

paper · doi:10.1002/anie.201107375

openalex publication_date 2011/12/15 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

High selectivity: A highly diastereo- and enantioselective Mannich reaction between a synthetically flexible ketimine and aldehydes has been developed. The syn- or anti-Mannich products contain tetrasubstituted chiral carbon centers and were obtained with almost complete stereoselectivity by using either L-proline or an axially chiral aminosulfonamide, respectively, as the catalyst (see scheme, Tf=trifluoromethanesulfonyl).

Cited by

• Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters
• Biocatalytic asymmetric Mannich reaction of ketimines using wheat germ lipase
• Construction of chiral α- tert -amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
• Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst
• Direct Organocatalytic Asymmetric Mannich Addition of 3‐Substituted‐2H‐1,4‐Benzoxazines: Access to Tetrasubstituted Carbon Stereocenters
• Ketimine Mannich reaction [wikipedia]

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