Asymmetric Mannich Reaction of α-(2-Nitrophenylsulfenyl)imino Acetamide: A Cyclization-Driven Process.

Tsubasa Inokuma, Maki Miyamoto, Kazuki Okada, Genki Nagai, Ken-Ichi Yamada

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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0citing papers in PubMed

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1 · What the graph read from it

What it found

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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

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0 citing papers in PubMed.

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4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Tsubasa InokumaGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.ORCID 0000-0002-2331-2758

Maki MiyamotoGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.

Kazuki OkadaGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.

Genki NagaiGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.

Ken-Ichi YamadaGraduate School of Pharmaceutical Sciences, Tokushima University, Shomachi, Tokushima 770-8505, Japan.ORCID 0000-0002-4136-0761

Funding

Fugaku Trust for Medicinal Research not availableJapan Society for the Promotion of Science JP24H01320the Mochida Memorial Foundation for Medical and Pharmaceutical Research not availableTokushima University Research Clusters Programs no. 2201004Tokushima University Research Clusters Programs no. 2402001

6 · The paper itself

Abstract

An enantioselective Mannich reaction of 2-(2-nitrophenylsulfenylimino)acetamide is described. Under the optimized conditions using proline, triethylamine, and diarylthiourea additives, the initially formed Mannich adduct undergoes irreversible cyclization to afford cyclic hemiaminal products in 21-58% yield, with diastereomeric ratios ranging from 53:47 to 83:17. Enantioselectivity reaches up to 97% ee. The presence of N-H functionality of the substrate is crucial for this cyclization; in its absence, the Mannich adduct undergoes facile decomposition. Subsequent reduction in this intermediate efficiently furnished the corresponding homoserine derivative.

Indexed as

cyclic hemiaminalhomoserineimino acetamideMannich reactionorganocatalysispeptideprolinethiourea

Identifiers

PMID41683426

DOI10.3390/molecules31030449

PMCPMC12899788

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.