Evidence map›Paper›PMID 39875325›Full record

ArticleAngewandte Chemie (International ed. in English)2025

Enantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.

Jonathan Bajohr, Shangyu Li, Bijan Mirabi, Colton E Johnson, Mark Lautens

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. Enantioselective Borylcupration/Cyclization of Alkene-Tethered Oxime Esters.Angewandte Chemie (International ed. in English) · 2025
    Article
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.

Jonathan BajohrDepartment of Chemistry, University of Toronto, 80 St George St, Toronto, ON M5S 3H6, Canada.ORCID https://orcid.org/0000-0003-1948-9320
Shangyu LiDepartment of Chemistry, University of Toronto, 80 St George St, Toronto, ON M5S 3H6, Canada.
Bijan MirabiDepartment of Chemistry, University of Toronto, 80 St George St, Toronto, ON M5S 3H6, Canada.ORCID https://orcid.org/0000-0002-4852-3439
Colton E JohnsonDepartment of Chemistry, University of Toronto, 80 St George St, Toronto, ON M5S 3H6, Canada.ORCID https://orcid.org/0000-0002-0905-1248
Mark LautensDepartment of Chemistry, University of Toronto, 80 St George St, Toronto, ON M5S 3H6, Canada.ORCID https://orcid.org/0000-0002-0179-2914

Funding

Kennarshore Inc.Natural Science and Engineering Research Council (NSERC)Paraza Pharma Inc.University of Toronto
6 · The paper itself

Abstract

A copper-catalyzed enantioselective synthesis of borylated 1-pyrrolines from γ,δ-unsaturated oxime esters is reported. Twenty-four novel 1-pyrroline derivatives are reported in yields ranging from 26% to 96% and enantioselectivities from 74.5:25.5 er to 99:1 er. Examples derived from α-unsubstituted, non-fluorinated oxime esters are reported. The hydroxyl group following oxidation of the Bpin moiety acts as a directing group in highly diastereoselective reductions of the pyrrolines to the corresponding prolinol derivatives. Additionally, the Bpin group can be retained in the products following a simplified, chromatography-free workup procedure. DFT supports a reaction mechanism which proceeds through the formation of an (R)-benzylic copper intermediate, followed by stereoretentive cyclization with respect to the configuration at the metalated carbon. The conclusions of the computational data are corroborated through control experiments and deuterium-labelling studies.

Indexed as

1-PyrrolinesAsymmetric CatalysisCopper Borylation

Identifiers

PMID39875325
PMCPMC11878337

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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.