Evidence map›Paper›PMID 37711191›Full record

ArticleACS catalysis2023

Mechanism of a Dually Catalyzed Enantioselective Oxa-Pictet-Spengler Reaction and the Development of a Stereodivergent Variant.

Alafate Adili, John-Paul Webster, Chenfei Zhao, Sharath Chandra Mallojjala, Moises A Romero-Reyes, Ion Ghiviriga, Khalil A Abboud, Mathew J Vetticatt, Daniel Seidel

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ACS catalysis, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Catalytic Enantioselective Synthesis of 1,1-Disubstituted Isochromans.Journal of the American Chemical Society · 2026
    Article
  2. Article
  3. 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.

Alafate AdiliCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
John-Paul WebsterDepartment of Chemistry, Binghamton University, Binghamton, New York 13902, United States.
Chenfei ZhaoDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.ORCID 0000-0003-3960-3047
Sharath Chandra MallojjalaDepartment of Chemistry, Binghamton University, Binghamton, New York 13902, United States.
Moises A Romero-ReyesCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Ion GhivirigaCenter for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0001-5812-5170
Khalil A AbboudCenter for X-ray Crystallography, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Mathew J VetticattDepartment of Chemistry, Binghamton University, Binghamton, New York 13902, United States.ORCID 0000-0001-5709-0885
Daniel SeidelDepartment of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID 0000-0001-6725-111X

Funding

Mechanistic Studies at the Frontiers of CatalysisR35GM145320 · NIGMS · STATE UNIVERSITY OF NY,BINGHAMTON · PI Mathew J Vetticatt · 2022 to 2026
$1.9M
400 MHz NMR Spectrometer for Regional NMR FacilityS10OD026746 · OD · STATE UNIVERSITY OF NY,BINGHAMTON · PI VETTICATT, MATHEW J · 2019 to 2019
$600k
Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
NIGMS NIH HHS R35 GM145320NIH HHS S10 OD021758NIH HHS S10 OD026746
6 · The paper itself

Abstract

Enantioselective oxa-Pictet-Spengler reactions of tryptophol with aldehydes proceed under weakly acidic conditions utilizing a combination of two catalysts, an indoline HCl salt and a bisthiourea compound. Mechanistic investigations revealed the roles of both catalysts and confirmed the involvement of oxocarbenium ion intermediates, ruling out alternative scenarios. A stereochemical model was derived from density functional theory calculations, which provided the basis for the development of a highly enantioselective stereodivergent variant with racemic tryptophol derivatives.

Indexed as

anion-binding catalysisasymmetric catalysisDFT calculationsdual catalysiskinetic isotope effectsoxa-Pictet–Spengler reactionoxocarbenium ions

Identifiers

PMID37711191
PMCPMC10501388

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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.