Evidence map›Paper›PMID 31794118›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins.

Raphael Bigler, Kyle A Mack, Jeff Shen, Paolo Tosatti, Chong Han, Stephan Bachmann, Haiming Zhang, Michelangelo Scalone, Andreas Pfaltz, Scott E Denmark and 2 more

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing 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

9 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

12 authors.

Raphael BiglerPharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.ORCID 0000-0003-1898-9112
Kyle A MackDepartment of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.
Jeff ShenDepartment of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.
Paolo TosattiPharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.
Chong HanDepartment of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.
Stephan BachmannPharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.
Haiming ZhangDepartment of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.
Michelangelo ScalonePharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.
Andreas PfaltzDepartment of Chemistry, University of Basel, 4056, Basel, Switzerland.
Scott E DenmarkRoger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
Stefan HildbrandPharmaceutical Division, Small Molecules Technical Development, Department of Process Chemistry and Catalysis, F. Hoffmann-La Roche Ltd, 4070, Basel, Switzerland.
Francis GosselinDepartment of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, CA, 94080, USA.

Funding

Organosilicon-Based Cross-Coupling ReactionsR01GM063167 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2002 to 2009
$2.5M
Asymmetric Lewis Base Catalysis in Main Group ChemistryR01GM085235 · NIGMS · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2010 to 2017
$2.4M
Synthetic and Mechanistic Studies on Preparatively Significant ReactionsR35GM127010 · NIGMS · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2018 to 2022
$2.2M
THE CYCLOADDITION CHEMISTRY OF NITROALKENESR01GM030938 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 1985 to 2007
$2.1M
NIGMS NIH HHS R01 GM030938NIGMS NIH HHS R01 GM063167NIGMS NIH HHS R01 GM085235NIGMS NIH HHS R35 GM127010
6 · The paper itself

Abstract

Asymmetric hydrogenation has evolved as one of the most powerful tools to construct stereocenters. However, the asymmetric hydrogenation of unfunctionalized tetrasubstituted acyclic olefins remains the pinnacle of asymmetric synthesis and an unsolved challenge. We report herein the discovery of an iridium catalyst for the first, generally applicable, highly enantio- and diastereoselective hydrogenation of such olefins and the mechanistic insights of the reaction. The power of this chemistry is demonstrated by the successful hydrogenation of a wide variety of electronically and sterically diverse olefins in excellent yield and high enantio- and diastereoselectivity.

Indexed as

asymmetric catalysishydrogenationiridiumN,P ligandstetrasubstituted olefins

Identifiers

PMID31794118
PMCPMC7141762

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.