Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.

Nicholas R Babij, Jordan R Boothe, Grace M McKenna, Ryan M Fornwald, John P Wolfe

Abstract read

In one paragraph

Article in Tetrahedron, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

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2citing 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

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3 · Its place in the literature

Who cites it

2 citing papers in PubMed.

Copper(I)-Catalyzed Cross-Coupling of 1-Bromoalkynes with N-Heterocyclic Organozinc Reagents.Molecules (Basel, Switzerland) · 2022
Article
Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.Israel journal of chemistry · 2020
Article

4 · The record

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5 · Who and what money

Authors and funding

5 authors.

Nicholas R BabijDepartment of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

Jordan R BootheDepartment of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

Grace M McKennaDepartment of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

Ryan M FornwaldDepartment of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

John P WolfeDepartment of Chemistry, University of Michigan, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA.

Funding

New Alkene Difunctionalization Reactions for Organic SynthesisR01GM098314 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI WOLFE, JOHN P · 2011 to 2014

$1.1M

NIGMS NIH HHS R01 GM098314

6 · The paper itself

Abstract

The synthesis of bicyclic ureas and sulfamides via palladium-catalyzed alkene carboamination reactions between aryl/alkenyl halides/triflates and alkenes bearing pendant cyclic sulfamides and ureas is described. The substrates for these reactions are generated in 3-5 steps from commercially available materials, and products are obtained in good yield with up to >20:1 diastereoselectivity. The stereochemical outcome of the sulfamide alkene addition is consistent with a mechanism involving

Indexed as

AlkenesHeterocyclesPalladiumStereoselective

Identifiers

PMID31866698

DOI10.1016/j.tet.2019.04.031

PMCPMC6924926

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