Stereocontrolled Ring-Opening of Oxazolidinone-Fused Aziridines for the Synthesis of 2-Amino Ethers.

Tsung-Lun Tsai, Chin-Hsun Wu, Chih-Ling Lo, Chi-Sheng Wen, Duen-Ren Hou

Abstract read

In one paragraph

Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

0numbers the graph read from it

0cells of the map it votes in

0citing papers in PubMed

–field-weighted citation impact

1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

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

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

0 citing papers in PubMed.

No citing paper in PubMed yet.

4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

5 authors.

Tsung-Lun TsaiDepartment of Chemistry, National Central University, 300 Jhong-Da Rd., Jhong-Li, Taoyuan 320317, Taiwan.

Chin-Hsun WuDepartment of Chemistry, National Central University, 300 Jhong-Da Rd., Jhong-Li, Taoyuan 320317, Taiwan.

Chih-Ling LoDepartment of Chemistry, National Central University, 300 Jhong-Da Rd., Jhong-Li, Taoyuan 320317, Taiwan.

Chi-Sheng WenDepartment of Chemistry, National Central University, 300 Jhong-Da Rd., Jhong-Li, Taoyuan 320317, Taiwan.

Duen-Ren HouDepartment of Chemistry, National Central University, 300 Jhong-Da Rd., Jhong-Li, Taoyuan 320317, Taiwan.ORCID 0000-0003-1072-2915

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report a stereocontrolled method for synthesizing 2-amino ethers via the acid-catalyzed ring-opening of oxazolidinone-fused aziridines with alcohols. Mono-, di-, and trisubstituted aziridines all participate in this transformation, with the substitution pattern and the class of alcohol significantly influencing the outcome. High diastereoselectivity was observed with primary and secondary alcohols, while tertiary alcohols often led to elimination or epimerization, depending on the aziridine substrate. This methodology was further applied to the synthesis of the neuraminidase inhibitor A-315675. This method offers a broad scope and high diastereoselectivity in many cases, making it a useful strategy for the construction of 2-amino ether frameworks.

Identifiers

PMID40622865

DOI10.1021/acs.joc.5c01068

PMCPMC12281577

What OpenQuestion holds

Textmetadata

LicenceCC BY

Read underepoch 390

Registered trials

None linked

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.