Diastereoselective Substitution Reactions of Acyclic Acetals Controlled by Remote Participation of an Acyloxy Group.

Khoi B Luu, Amanda Ramdular, Eli Finkelstein, Alexander G Shtukenberg, K A Woerpel

Abstract read

In one paragraph

Article in Organic letters, 2024. 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.

Photocatalytic construction ofChemical science · 2026
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.

Khoi B LuuDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0003-3286-1983

Amanda RamdularDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.

Eli FinkelsteinDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.

Alexander G ShtukenbergDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-5590-4758

K A WoerpelDepartment of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.ORCID 0000-0002-8515-0301

Funding

Stereoselective Reactions of Oxocarbenium Ions and Related IntermediatesR35GM148203 · NIGMS · NEW YORK UNIVERSITY · PI KEITH ALLEN WOERPEL · 2023 to 2026

$1.9M

Acquisition of a Cryoprobe for a 600 MHz NMR SpectrometerS10OD016343 · OD · NEW YORK UNIVERSITY · PI KROGSGAARD, MICHELLE, TRAASETH, NATHANIEL J. · 2014 to 2014

$360k

NIGMS NIH HHS R35 GM148203NIH HHS S10 OD016343

6 · The paper itself

Abstract

A remote carbonyl group up to six atoms away from the acetal group can induce 1,2-asymmetric induction in nucleophilic substitution reactions of acyclic acetals. Isolation of a cyclic carbonate under Lewis acidic conditions and computational studies suggested that the remote carbonyl group participated through the formation of a cyclic dioxocarbenium ion intermediate. The stereochemical outcomes depended on the size of the alkyl substituent and that of the nucleophile employed.

Identifiers

PMID39622244

DOI10.1021/acs.orglett.4c03766

PMCPMC11650769

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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.