Evidence map›Paper›PMID 34487418›Full record

ArticleAngewandte Chemie (International ed. in English)2021

Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes.

Yuk-Cheung Chan, Marcus H Sak, Scott A Frank, Scott J Miller

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
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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

4 authors.

Yuk-Cheung ChanDepartment of Chemistry, Yale University, New Haven, CT, 06520, USA.ORCID 0000-0003-0518-1990
Marcus H SakDepartment of Chemistry, Yale University, New Haven, CT, 06520, USA.ORCID 0000-0001-5691-4459
Scott A FrankSynthetic Molecule Design and Development, Eli Lilly and Company, Indianapolis, IN, 46285, USA.ORCID 0000-0001-6680-9695
Scott J MillerDepartment of Chemistry, Yale University, New Haven, CT, 06520, USA.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
eli lilly and companyNIGMS NIH HHS R35 GM132092NIH HHS R35 GM132092
6 · The paper itself

Abstract

Herein we report an organocatalytic enantioselective functionalization of heterocyclic carboxaldehydes via the Pictet-Spengler reaction. Through careful pairing of novel squaramide and Brønsted acid catalysts, our method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated β-(tetrahydro)carbolines in good yield and enantioselectivity. Careful selection of carboxylic acid co-catalyst is essential for toleration of a variety of regioisomeric heterocycles. Utility is demonstrated via the three-step stereoselective preparation of pyridine-containing analogues of potent selective estrogen receptor downregulator and U.S. FDA approved drug Tadalafil.

Indexed as

AldehydesBenzaldehydesCarbolinesCarboxylic AcidsCatalysisHeterocyclic CompoundsHydrogen BondingNitrogenStereoisomerism3-pyridinaldehydeAldehydesbenzaldehydeBenzaldehydesCarbolinesCarboxylic AcidsHeterocyclic CompoundsNitrogencooperative catalysisheterocycleshydrogen bond donorspeptidesPictet-Spengler

Identifiers

PMID34487418
PMCPMC8556314

What OpenQuestion holds

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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.