Literature DB >> 34518847

Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.

Ilyas A Berhane1, Ameya S Burde1, Jonathan J Kennedy-Ellis1, Eva Zurek1, Sherry R Chemler1.   

Abstract

The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1 receptor ligand using this alkene carboetherification methodology was demonstrated. Ligand, solvent and base all impact reaction efficiency. DFT transition state calculations are presented.

Entities:  

Year:  2021        PMID： 34518847      PMCID： PMC8590114          DOI： 10.1039/d1cc03515k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.065


  25 in total

1.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy.

Authors:  Florian Weigend; Reinhart Ahlrichs
Journal:  Phys Chem Chem Phys       Date:  2005-08-04       Impact factor: 3.676

2.  Density functionals with broad applicability in chemistry.

Authors:  Yan Zhao; Donald G Truhlar
Journal:  Acc Chem Res       Date:  2008-01-11       Impact factor: 22.384

3.  Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions.

Authors:  Aleksandr V Marenich; Christopher J Cramer; Donald G Truhlar
Journal:  J Phys Chem B       Date:  2009-05-07       Impact factor: 2.991

4.  Synthesis of Spirocyclic Ethers by Enantioselective Copper-Catalyzed Carboetherification of Alkenols.

Authors:  Shuklendu D Karyakarte; Chanchamnan Um; Ilyas A Berhane; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-03       Impact factor: 15.336

5.  Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction.

Authors:  Tejas P Pathak; Keith M Gligorich; Bryan E Welm; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

6.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

7.  Recent advances in copper-catalysed radical-involved asymmetric 1,2-difunctionalization of alkenes.

Authors:  Zhong-Liang Li; Gui-Chun Fang; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Chem Soc Rev       Date:  2020-01-02       Impact factor: 54.564

8.  Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes.

Authors:  Guozhu Zhang; Li Cui; Yanzhao Wang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

9.  Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions.

Authors:  Naifu Hu; Ke Li; Zheng Wang; Wenjun Tang
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-16       Impact factor: 15.336

10.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

Authors:  Dake Chen; Sherry R Chemler
Journal:  Org Lett       Date:  2018-10-11       Impact factor: 6.005
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