Evidence map›Paper›PMID 34881491›Full record

ArticleAngewandte Chemie (International ed. in English)2022

A Mechanistically Inspired Halenium Ion Initiated Spiroketalization: Entry to Mono- and Dibromospiroketals.

Kumar Dilip Ashtekar, Hadi Gholami, Mehdi Moemeni, Ankush Chakraborty, Lindsey Kiiskila, Xinliang Ding, Edmond Toma, Christopher Rahn, Babak Borhan

Open access · greenAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.4field-weighted citation impact, top 42% of its field
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

2 citing papers in PubMed, 6 citations in OpenAlex.

  1. Article
  2. 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

9 authors at 2 institutions in 1 country.

Kumar Dilip AshtekarCancer Biology Institute, Yale School of Medicine, West Haven, Connecticut, 06516, USA.ORCID 0000-0001-8264-6558
Hadi GholamiDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.ORCID 0000-0001-6520-0845
Mehdi MoemeniDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Ankush ChakrabortyDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Lindsey KiiskilaDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Xinliang DingDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Edmond TomaDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Christopher RahnDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Babak BorhanDepartment of Chemistry, Michigan State University, East Lansing, MI 48824, USA.ORCID 0000-0002-3193-0732
Michigan State University · USYale Cancer Center · US

Funding

Predicted Reaction Discovery and Application of Catalytic Asymmetric Alkene HalogenationsR01GM110525 · NIGMS · MICHIGAN STATE UNIVERSITY · PI BORHAN, BABAK · 2014 to 2018
$1.0M
NIGMS NIH HHS R01 GM110525
6 · The paper itself

Abstract

Employing halenium affinity (HalA) as a guiding tool, the weak nucleophilic character of alkyl ketones was modulated by the templating effect of a tethered 2-tetrahydropyranyl(THP)-protected alcohol towards realizing a bromenium ion initiated spiroketalization cascade. Addition of ethanol aided an early termination of the cascade by scavenging the THP group after the halofunctionalization stage, furnishing monobromospiroketals. Alternatively, exclusion of ethanol from the reaction mixture biased the transient oxocarbenium towards α-deprotonation that precedes a second bromofunctionalization event thus, furnishing dibrominated spiroketals. The regio- and stereoselectivity exploited in the current methodology provides a novel and rapid access to the dibrominated spiroketal motifs exhibited by several natural products.

Indexed as

BromineFuransIonsMolecular StructureSpiro CompoundsStereoisomerismBromineFuransIonsSpiro CompoundsspiroketalHalenium affinityHalocyclizationReaction mechanismsSpiroketalization

Identifiers

PMID34881491
PMCPMC9254888
OpenAlexW4200538406

What OpenQuestion holds

Textmetadata
LicenceTDM
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.