Evidence map›Paper›PMID 32598506›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry.

Sheng Guo, Jiaqi Zhu, Stephen L Buchwald

Open access · greenAbstract 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 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
2.0field-weighted citation impact, top 13% of its field
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, 38 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Improving regioselectivity of phenylalanine aminomutase fromFrontiers in bioengineering and biotechnology · 2024
    Article
  5. Application of Biobased Solvents in Asymmetric Catalysis.Molecules (Basel, Switzerland) · 2022
    Review
  6. Article
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

3 authors at 1 institution in 1 country.

Sheng GuoDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.ORCID 0000-0002-2542-0525
Jiaqi ZhuDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 02139, USA.ORCID 0000-0003-3875-4775
Massachusetts Institute of Technology · US

Funding

Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R35 GM122483NIH HHS R35-GM122483
6 · The paper itself

Abstract

A Cu-catalyzed enantioselective hydroamination of α,β-unsaturated carbonyl compounds for the synthesis of β-amino acid derivatives was achieved through ligand-controlled reversal of the hydrocupration regioselectivity. While the hydrocupration of α,β-unsaturated carbonyl compounds to form α-cuprated species has been extensively investigated, we report herein that, in the presence of an appropriate ancillary chiral ligand, the opposite regiochemistry can be observed for cinnamic acid derivatives, leading to the delivery of the copper to the β-position. This copper can react with an electrophilic aminating reagent, 1,2-benzisoxazole, to provide enantioenriched β-amino acid derivatives, which are important building blocks for the synthesis of natural products and bioactive small molecules.

Indexed as

AminationAmino AcidsCatalysisCopperLigandsMolecular StructureStereoisomerismAmino AcidsCopperLigandsasymmetric synthesiscopperhydroaminationregioselectivityβ-amino acids

Identifiers

PMID32598506
PMCPMC8038868
OpenAlexW3037048912

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.