Evidence map›Paper›PMID 28560721›Full record

ArticleAngewandte Chemie (International ed. in English)2017

Electronically Activated Organoboron Catalysts for Enantioselective Propargyl Addition to Trifluoromethyl Ketones.

Nicholas W Mszar, Malte S Mikus, Sebastian Torker, Fredrik Haeffner, Amir H Hoveyda

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 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

5 authors.

Nicholas W MszarDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
Malte S MikusDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
Sebastian TorkerDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
Fredrik HaeffnerDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
Amir H HoveydaDepartment of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.ORCID 0000-0002-1470-6456

Funding

NEW CATALYTIC AND ENANTIOSELECTIVE REACTIONSR01GM057212 · NIGMS · BOSTON COLLEGE · PI HOVEYDA, AMIR H · 1998 to 2017
$5.7M
NIGMS NIH HHS R01 GM057212
6 · The paper itself

Abstract

A broadly applicable, practical, scalable, efficient and highly α- and enantioselective method for addition of a silyl-protected propargyl moiety to trifluoromethyl ketones has been developed. Reactions, promoted by 2.0 mol % of a catalyst that is derived in situ from a readily accessible aminophenol compound at ambient temperature, were complete after only 15 minutes at room temperature. The desired tertiary alcohols were isolated in up to 97 % yield and 98.5:1.5 enantiomeric ratio. Alkyl-, alkenyl-, alkynyl-, aryl- or heteroaryl-substituted trifluoromethyl ketones can be used. Utility is highlighted by application to a transformation that is relevant to enantioselective synthesis of BI 653048, a compound active against rheumatoid arthritis.

Indexed as

Arthritis, RheumatoidBenzamidesBoron CompoundsCatalysisElectronicsKetonesMolecular StructureMorphinansPyridinesPyrrolesStereoisomerismBenzamidesBI 653048 BS H3PO4Boron CompoundsKetonesMorphinansN-propargylPyridinesPyrrolescatalysisenantioselective synthesishomopropargylic alcoholspropargyl groupstrifluoromethyl group

Identifiers

PMID28560721
PMCPMC5535737

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.