Literature DB >> 25111560

Gold-catalyzed 1,2-acyloxy migration/intramolecular [3+2] 1,3-dipolar cycloaddtion cascade reaction: an efficient strategy for syntheses of medium-sized-ring ethers and amines.

Changgui Zhao1, Xingang Xie, Shuangshuang Duan, Huilin Li, Ran Fang, Xuegong She.   

Abstract

A highly efficient strategy for the formation of medium-sized-ring ethers and amines based on a gold-catalyzed cascade reaction, involving enynyl ester isomerization and intramolecular [3+2] cyclization, has been developed. Various multisubstituted medium-sized-ring unsaturated ethers and amines were obtained through this transformation. This method represents one of the relatively few transition metal catalyzed intramolecular cycloaddition reactions for medium-sized ring synthesis.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloaddition; gold; heterocycles; medium-ring compounds; synthetic methods

Mesh:

Substances:

Year:  2014        PMID: 25111560     DOI: 10.1002/anie.201406486

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


  5 in total

1.  Formal Synthesis of (+)-Laurencin by Gold(I)-Catalyzed Intramolecular Dehydrative Alkoxylation.

Authors:  Megan L Lanier; Hyeri Park; Paramita Mukherjee; Jacob C Timmerman; Anthony A Ribeiro; Ross A Widenhoefer; Jiyong Hong
Journal:  Chemistry       Date:  2017-05-03       Impact factor: 5.236

2.  Gold-Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters.

Authors:  Peng-Long Zhu; Xiang-Ying Tang; Min Shi
Journal:  ChemistryOpen       Date:  2015-10-12       Impact factor: 2.911

Review 3.  Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization.

Authors:  Mickael Choury; Alexandra Basilio Lopes; Gaëlle Blond; Mihaela Gulea
Journal:  Molecules       Date:  2020-07-09       Impact factor: 4.411

4.  Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition-Fragmentation Strategy.

Authors:  Megan H Shaw; Rosemary A Croft; William G Whittingham; John F Bower
Journal:  J Am Chem Soc       Date:  2015-06-19       Impact factor: 15.419

5.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

  5 in total

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