Enantioselective Mannich Reactions of γ,δ-Unsaturated β-Keto Esters and Application in the Synthesis of β’-Amino enones, 2,6-Disubstituted Piperidin-4-ones and (+)-241D

Seerat Virk; Shaikh S. Nawaz; Sunil V. Pansare

doi:10.1021/acs.orglett.5c05199

Enantioselective Mannich Reactions of γ,δ-Unsaturated β-Keto Esters and Application in the Synthesis of β’-Amino enones, 2,6-Disubstituted Piperidin-4-ones and (+)-241D

Organic Letters 2026

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Authors: Seerat Virk, Shaikh S. Nawaz, Sunil V. Pansare

DOI: 10.1021/acs.orglett.5c05199

Cited by: 0

References: 41

Abstract

Enantioselective, organocatalytic Mannich reactions of γ,δ-unsaturated β-keto esters were developed. The Mannich products are readily decarboxylated to the corresponding amino enones, which can be cyclized to enantiomerically enriched 2,6-disubstituted piperidin-4-ones. The strategy is applied in a synthesis of the dendrobatid alkaloid (+)-241 D. Stereoselective reduction of a Mannich product provides a functionalized allylic alcohol with three contiguous stereocenters.

Fields of Study & Subjects

Asymmetric Synthesis and Catalysis Advanced Synthetic Organic Chemistry Synthesis and pharmacology of benzodiazepine derivatives

Publication details

Journal / source: Organic Letters
Volume: 28
Issue: 2
Pages: 884–888
Publication date: 2 January 2026
Language: EN

References 41