Literature DB >> 24874093

Palladium-catalyzed dearomative trimethylenemethane cycloaddition reactions.

Barry M Trost1, Veronika Ehmke, B Michael O'Keefe, Dustin A Bringley.   

Abstract

A general protocol for the palladium-catalyzed dearomative trimethylenemethane [3+2] cycloaddition reaction with simple nitroarene substrates is described. This methodology leads to the exclusive formation of the dearomatized alicyclic products without subsequent rearomatization. The reaction is tolerant toward a broad range of heterocyclic and benzenoid substrates. The use of chiral bisdiamidophosphite ligands enabled the development of an enantioselective variant of this transformation, representing one of the rare examples of an asymmetric catalytic dearomatization process.

Entities:  

Mesh:

Substances:

Year:  2014        PMID: 24874093     DOI: 10.1021/ja5044825

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

1.  Arenophile-Mediated Dearomative Reduction.

Authors:  Mikiko Okumura; Stephanie M Nakamata Huynh; Jola Pospech; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2016-11-23       Impact factor: 15.336

2.  Photochemical intermolecular dearomative cycloaddition of bicyclic azaarenes with alkenes.

Authors:  Jiajia Ma; Shuming Chen; Peter Bellotti; Renyu Guo; Felix Schäfer; Arne Heusler; Xiaolong Zhang; Constantin Daniliuc; M Kevin Brown; Kendall N Houk; Frank Glorius
Journal:  Science       Date:  2021-03-25       Impact factor: 47.728

3.  Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes.

Authors:  Ping Yang; Chao Zheng; Yu-Han Nie; Shu-Li You
Journal:  Chem Sci       Date:  2020-06-10       Impact factor: 9.825

Review 4.  Advances in Catalytic Asymmetric Dearomatization.

Authors:  Chao Zheng; Shu-Li You
Journal:  ACS Cent Sci       Date:  2021-02-22       Impact factor: 14.553

5.  Metal-Free Diastereo- and Enantioselective Dearomative Formal [3 + 2] Cycloaddition of 2-Nitrobenzofurans and Isocyanoacetate Esters.

Authors:  Adrian Laviós; Amparo Sanz-Marco; Carlos Vila; M Carmen Muñoz; José R Pedro; Gonzalo Blay
Journal:  Org Lett       Date:  2022-03-16       Impact factor: 6.005

6.  Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes.

Authors:  Song Yang; Quan-Zhe Li; Chen Xu; Qin Xu; Min Shi
Journal:  Chem Sci       Date:  2018-05-11       Impact factor: 9.825

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.