Evidence map›Paper›PMID 39928956›Full record

ArticleOrganic letters2025

Stereoselective Synthesis of Highly Functionalized Bicyclo[2.1.0]pentanes by Sequential [2 + 1] and [2 + 2] Cycloadditions.

Brockton Keen, Christina Cong, Alberto Castanedo, Geraint H M Davies, Robert R Knowles, Huw M L Davies

Abstract read
In one paragraph

Article in Organic letters, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

  1. Article
  2. Stereocontrolled Synthesis of Polysubstituted Housanes viaJournal of the American Chemical Society · 2026
    Article
  3. Cyclopropenes in Photochemical Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026
    Review
  4. Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes.Journal of the American Chemical Society · 2025
    Article
  5. Article
  6. Catalytic Oxidative Ligand Transfer of Rh-Carbynoids and Alkyl Iodides.Journal of the American Chemical Society · 2025
    Article
  7. Article
  8. 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

6 authors.

Brockton KeenDepartment of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
Christina CongDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Alberto CastanedoDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0001-5048-0258
Geraint H M DaviesPostEra, One Broadway, 14th Floor, Cambridge, Massachusetts 02142, United States.ORCID 0000-0002-5986-0756
Robert R KnowlesDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-1044-4900
Huw M L DaviesDepartment of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.ORCID 0000-0001-6254-9398

Funding

N-Sulfonyltriazoles as Carbene PrecursorsR01GM099142 · NIGMS · EMORY UNIVERSITY · PI DAVIES, HUW M · 2011 to 2023
$4.1M
New Synthetic Methods Enabled by Excited-State Redox ChemistryR35GM134893 · NIGMS · PRINCETON UNIVERSITY · PI Robert R Knowles · 2020 to 2026
$3.8M
NIGMS NIH HHS R01 GM099142NIGMS NIH HHS R35 GM134893
6 · The paper itself

Abstract

This study describes a method for the stereoselective synthesis of highly functionalized bicyclo[2.1.0]pentanes (housanes). The approach utilizes a two-step sequence, a silver- or gold-catalyzed cyclopropenation of alkynes followed by an intermolecular [2 + 2] photocycloaddition reaction with electron-deficient alkenes. The cyclopropenation is an established reaction of aryldiazoacetates. A regioselective [2 + 2] cycloaddition of the cyclopropane was developed using blue LED irradiation, a commercially available photocatalyst as a triplet-sensitizer, and low reaction temperature (-40 °C). The [2 + 2] cycloaddition is highly diastereoselective, and when enantioenriched cyclopropenes are used, it proceeds with enantioretention.

Identifiers

PMID39928956
PMCPMC11852226

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Registered trials

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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.