Evidence map›Paper›PMID 28970901›Full record

ArticleChemical science2017

Enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes.

Jiawang Liu, Ming Nie, Qinghai Zhou, Shen Gao, Wenhao Jiang, Lung Wa Chung, Wenjun Tang, Kuiling Ding

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Article
  2. Catalytic Enantioselective Diboration of 1,2-Dihydropyridines.Angewandte Chemie (International ed. in English) · 2025
    Article
  3. Enantioselective Copper-Catalyzed spACS central science · 2022
    Article
  4. Review
  5. 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

8 authors.

Jiawang LiuState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.ORCID 0000-0002-8548-6286
Ming NieState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.
Qinghai ZhouDepartment of Chemistry , South University of Science and Technology of China , Shenzhen 518055 , China . Email: oscarchung@sustc.edu.cn.
Shen GaoState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.
Wenhao JiangState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.
Lung Wa ChungDepartment of Chemistry , South University of Science and Technology of China , Shenzhen 518055 , China . Email: oscarchung@sustc.edu.cn.ORCID 0000-0001-9460-7812
Wenjun TangState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.ORCID 0000-0002-8209-4156
Kuiling DingState Key Laboratory of Organometallic Chemistry , State Key Laboratory of Bio-Organic and Natural Products Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Ling Ling Rd , Shanghai 200032 , China . Email: tangwenjun@sioc.ac.cn ; Email: kding@sioc.ac.cn.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A practical and enantioselective palladium-catalyzed diboration of 1,1-disubstituted allenes is developed by employing a P-chiral monophosphorus ligand, BI-DIME. A series of diboronic esters containing a chiral tertiary boronic ester moiety are formed in excellent yields and ee's with the palladium loading as low as 0.2 mol%. DFT calculations revealed a concerted mechanism of oxidative addition of bis(pinacolato)diboron and allene insertion, as well as a critical dispersion effect on the origins of the enantioselectivity. The method is successfully applied to the concise and enantioselective synthesis of brassinazole.

Identifiers

PMID28970901
PMCPMC5615263

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