Evidence map›Paper›PMID 27065720›Full record

ArticleOrganic process research & development2016

Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Brønsted Acid-Base Catalyst with Recycle.

Sergey V Tsukanov, Martin D Johnson, Scott A May, Morgan Rosemeyer, Michael A Watkins, Stanley P Kolis, Matthew H Yates, Jeffrey N Johnston

Abstract read
In one paragraph

Article in Organic process research & development, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.

0numbers the graph read from it
0cells of the map it votes in
8citing 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

8 citing papers in PubMed.

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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

8 authors.

Sergey V TsukanovSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States; Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.
Martin D JohnsonSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Scott A MaySmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Morgan RosemeyerSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Michael A WatkinsSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Stanley P KolisSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Matthew H YatesSmall Molecule Design and Development, Eli Lilly and Company, Indianapolis, Indiana 46285, Unites States.
Jeffrey N JohnstonDepartment of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States.

Funding

New Stereoselective Reactions for Chiral Amine SynthesisR01GM084333 · NIGMS · VANDERBILT UNIVERSITY · PI JOHNSTON, JEFFREY NICHOLAS · 2009 to 2017
$2.2M
NIGMS NIH HHS R01 GM084333
6 · The paper itself

Abstract

A stereoselective aza-Henry reaction between an arylnitromethane and Boc-protected aryl aldimine using a homogeneous Brønsted acid-base catalyst was translated from batch format to an automated intermittent-flow process. This work demonstrates the advantages of a novel intermittent-flow setup with product crystallization and slow reagent addition which is not amenable to the standard continuous equipment: plug flow tube reactor (PFR) or continuous stirred tank reactor (CSTR). A significant benefit of this strategy was the integration of an organocatalytic enantioselective reaction with straightforward product separation, including recycle of the catalyst, resulting in increased intensity of the process by maintaining high catalyst concentration in the reactor. A continuous campaign confirmed that these conditions could effectively provide high throughput of material using an automated system while maintaining high selectivity, thereby addressing nitroalkane safety and minimizing catalyst usage.

Indexed as

asymmetric catalysis or synthesisaza-Henry reactioncontinuous processesflow chemistryorganocatalysissustainable or green chemistry

Identifiers

PMID27065720
PMCPMC4821467

What OpenQuestion holds

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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.