Evidence map›Paper›PMID 39847512›Full record

ArticleJournal of the American Chemical Society2025

Enantiocontrolled Cyclization to Form Chiral 7- and 8-Membered Rings Unified by the Same Catalyst Operating with Different Mechanisms.

Nicolò Tampellini, Brandon Q Mercado, Scott J Miller

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.

0numbers the graph read from it
0cells of the map it votes in
7citing 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

7 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Review
  7. London Dispersion as a Design Element in Molecular Catalysis.Journal of the American Chemical Society · 2025
    Review
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

3 authors.

Nicolò TampelliniDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.ORCID 0000-0002-6611-556X
Brandon Q MercadoDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.
Scott J MillerDepartment of Chemistry, Yale University, New Haven, Connecticut 06520, United States.ORCID 0000-0001-7817-1318

Funding

Site-Selective Catalysis for Bioactive Scaffold DiversificationR35GM132092 · NIGMS · YALE UNIVERSITY · PI Scott J Miller · 2019 to 2026
$6.3M
NIGMS NIH HHS R35 GM132092
6 · The paper itself

Abstract

Chiral medium-sized rings, albeit displaying attractive properties for drug development, suffer from numerous synthetic challenges due to difficult cyclization steps that must take place to form these unusually strained, atropisomeric rings from sterically crowded precursors. In fact, catalytic enantioselective cyclization methods for the formation of chiral seven-membered rings are unknown, and the corresponding eight-membered variants are also sparse. In this work, we present a substrate preorganization-based, enantioselective, organocatalytic strategy to construct seven- and eight-membered rings featuring chirality that is intrinsic to the ring in the absence of singular stereogenic atoms or single bond axes of chirality. The reactions proceed under mild conditions and with high levels of stereocontrol. Notably, the same bifunctional iminophosphorane chiral catalyst orchestrates the cyclization of substrates of two different ring sizes, under two different mechanistic paradigms. We envision that the mechanistic and ring size versatility of this method could guide further applications of asymmetric catalysis to other challenging cyclization reactions.

Identifiers

PMID39847512
PMCPMC11815475

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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.