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. 2023 Aug 4;88(15):11096-11101.
doi: 10.1021/acs.joc.3c01051. Epub 2023 Jul 17.

1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones

Yuvraj Garg  1 , James Osborne  1 , Serhii Vasylevskyi  2 , Nivedha Velmurugan  1 , Fujie Tanaka  1
Affiliations

1,3-Diamine-Derived Catalysts: Design, Synthesis, and the Use in Enantioselective Mannich Reactions of Ketones

Yuvraj Garg et al. J Org Chem. .

Abstract

1,3-Diamine-derived catalysts were designed, synthesized, and used in asymmetric Mannich reactions of ketones. The reactions catalyzed by one of the 1,3-diamine derivatives in the presence of acids afforded the Mannich products with high enantioselectivities under mild conditions. In most cases, bond formation occurred at the less-substituted α-position of the ketone carbonyl group. Our results indicate that the primary and the tertiary amines of the 1,3-diamine derivative cooperatively act for the catalysis.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. 1,3-Diamine-Derived Catalyst Developed in This Work and the Asymmetric Mannich Reactions of Ketones
Scheme 2
Scheme 2. Synthesis of 1a
Scheme 3
Scheme 3. (a) Time Course Analysis of the Catalyzed Reactions, (b) Evaluation of the Stability of 10a under the Catalytic Conditions, and (c) Evaluation of the Stability of 9a under the Catalytic Conditions
Scheme 4
Scheme 4. Transformations of 9a
See this image and copyright information in PMC

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