Evidence map›Paper›PMID 35916601›Full record

ArticleAngewandte Chemie (International ed. in English)2022

Diastereoselective, Catalytic Access to Cross-Aldol Products Directly from Esters and Lactones.

Adrián Moreno González, Kieran Nicholson, Natalia Llopis, Gary S Nichol, Thomas Langer, Alejandro Baeza, Stephen P Thomas

Open access · hybridAbstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing papers in PubMed
1.4field-weighted citation impact, top 20% 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

4 citing papers in PubMed, 13 citations in OpenAlex.

  1. Article
  2. Group 13 exchange and transborylation in catalysis.Beilstein journal of organic chemistry · 2023
    Review
  3. Article
  4. 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

7 authors at 3 institutions in 4 countries.

Adrián Moreno GonzálezEaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK.
Kieran NicholsonEaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK.
Natalia LlopisEaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK.
Gary S NicholEaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK.
Thomas LangerAstraZeneca Pharmaceutical Technology & Development, Chemical Development UK, Silk Road, Macclesfield, SK10 2NA, UK.
Alejandro BaezaInstituto de Síntesis Orgánica and Dpto. de Química Orgánica, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain.
Stephen P ThomasEaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh, EH9 3FJ, UK.ORCID http://orcid.org/0000-0001-8614-2947
University of Edinburgh · GBAstraZeneca (United Kingdom) · GBUniversity of Alicante · ES

Funding

AstraZeneca
6 · The paper itself

Abstract

High oxidation-state carbonyl coupling partners including esters and lactones were reacted with enones to give aldol-type products directly using two-fold organoborane catalysis. This new retrosynthetic disconnection to aldol-type products is compatible with enolisable coupling partners, without self-condensation, and couples the high reactivity of secondary dialkylboranes with the stability of pinacolboronic esters. Excellent chemoselectivity, substrate scope (including those containing reducible functionalities and free alcohols) and diastereocontrol were achieved to access both the syn- and anti-aldol-type products. Mechanistic studies confirmed the two-fold catalytic role of the single secondary borane catalyst for boron enolate formation and formation of an aldehyde surrogate from the ester or lactone coupling partner.

Indexed as

AldolBoronC−C BondMain-Group CatalysisTransborylation

Identifiers

PMID35916601
PMCPMC9804986
OpenAlexW4289521056

What OpenQuestion holds

Textmetadata
LicenceCC BY
Read underepoch 390

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.