Literature DB >> 28370965

Asymmetric [4+2] Annulation of C1 Ammonium Enolates with Copper-Allenylidenes.

Jin Song1, Zi-Jing Zhang1, Liu-Zhu Gong1,2.   

Abstract

An asymmetric catalytic decarboxylative [4+2] annulation of 4-ethynyl dihydrobenzooxazinones and carboxylic acids has been established by cooperative copper and nucleophilic Lewis base catalysis. A C1 ammonium enolate and copper-allenylidene complex, each catalytically generated from different substrates, underwent a cascade asymmetric propargylation and lactamization process to yield optically active 3,4-dihydroquinolin-2-one derivatives with excellent levels of stereoselectivity (up to 99 % ee, 95:5 d.r.).
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C1 ammonium enolates; [4+2] annulations; cooperative catalysis; copper; heterocycles

Year:  2017        PMID： 28370965     DOI： 10.1002/anie.201700105

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Traversing Steric Limitations by Cooperative Lewis Base/Palladium Catalysis: An Enantioselective Synthesis of α-Branched Esters Using 2-Substituted Allyl Electrophiles.

Authors:  Kevin J Schwarz; Colin M Pearson; Gabriel A Cintron-Rosado; Peng Liu; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-18       Impact factor: 15.336

Review 3.  Scope and advances in the catalytic propargylic substitution reaction.

Authors:  Rashmi Roy; Satyajit Saha
Journal:  RSC Adv       Date:  2018-09-05       Impact factor: 3.361

4.  Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids.

Authors:  Teng Liu; Shaofei Ni; Wusheng Guo
Journal:  Chem Sci       Date:  2022-06-05       Impact factor: 9.969

5.  Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Authors:  Kevin J Schwarz; Chao Yang; James W B Fyfe; Thomas N Snaddon
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-20       Impact factor: 15.336

6.  Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls.

Authors:  Mao-Mao Zhang; Ya-Ni Wang; Bao-Cheng Wang; Xiao-Wang Chen; Liang-Qiu Lu; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2019-06-20       Impact factor: 14.919

7.  Two Catalytic Annulation Modes via Cu-Allenylidenes with Sulfur Ylides that Are Dominated by the Presence or Absence of Trifluoromethyl Substituents.

Authors:  Malla Reddy Gannarapu; Jun Zhou; Bingyao Jiang; Norio Shibata
Journal:  iScience       Date:  2020-03-20

8.  Synthesis of Tetra-Substituted Trifluoromethyl-3,1-Benzoxazines by Transition-Metal-Catalyzed Decarboxylative Cyclization of N-Benzoyl Benzoxazinones.

Authors:  Hiroto Uno; Daichi Fujimoto; Kyosuke Harada; Chika Tanaka; Norio Shibata
Journal:  ChemistryOpen       Date:  2021-02-19       Impact factor: 2.630

9.  Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.

Authors:  Dong-Sheng Ji; Hui Liang; Kai-Xuan Yang; Zhi-Tao Feng; Yong-Chun Luo; Guo-Qiang Xu; Yucheng Gu; Peng-Fei Xu
Journal:  Chem Sci       Date:  2022-01-18       Impact factor: 9.825

10.  Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.

Authors:  Stéphanie S M Spoehrle; Thomas H West; James E Taylor; Alexandra M Z Slawin; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.