Literature DB >> 23034723

Propargyl Claisen rearrangement: allene synthesis and beyond.

David Tejedor1, Gabriela Méndez-Abt, Leandro Cotos, Fernando García-Tellado.   

Abstract

The propargyl Claisen rearrangement is a known protocol to gain access to functionalized allenes through the [3,3]-sigmatropic transformation of propargyl vinyl ethers. The correct use of appropriate propargyl vinyl ethers as starting materials coupled with suitable reaction conditions can aid in the development of new domino methodologies in which the allenes are valuable intermediates in route to a wide range of important classes of organic compounds.

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Year:  2013        PMID: 23034723     DOI: 10.1039/c2cs35311c

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  7 in total

1.  Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.

Authors:  Jennifer A Dabrowski; Fredrik Haeffner; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

2.  Controlling, Understanding, and Redirecting the Thermal Rearrangement of 3,3-Dicyano-1,5-enynes.

Authors:  Sarah K Scott; Jacob N Sanders; Katherine E White; Roland A Yu; K N Houk; Alexander J Grenning
Journal:  J Am Chem Soc       Date:  2018-11-12       Impact factor: 15.419

3.  The 9H-Fluoren Vinyl Ether Derivative SAM461 Inhibits Bacterial Luciferase Activity and Protects Artemia franciscana From Luminescent Vibriosis.

Authors:  Alberto J Martín-Rodríguez; Sergio J Álvarez-Méndez; Caroline Overå; Kartik Baruah; Tânia Margarida Lourenço; Parisa Norouzitallab; Peter Bossier; Víctor S Martín; José J Fernández
Journal:  Front Cell Infect Microbiol       Date:  2018-11-08       Impact factor: 5.293

4.  Thioether-functionalized trifluoromethyl-alkynes, 1,3-dienes and allenes: divergent synthesis from reaction of 2-trifluoromethyl-1,3-conjugated enynes with sulfur nucleophiles.

Authors:  Huayu Cheng; Xiaofan Zhou; Anjing Hu; Shiteng Ding; Yimo Wang; Yuanjing Xiao; Junliang Zhang
Journal:  RSC Adv       Date:  2018-10-04       Impact factor: 4.036

Review 5.  Radical transformations for allene synthesis.

Authors:  Yajun Li; Hongli Bao
Journal:  Chem Sci       Date:  2022-06-29       Impact factor: 9.969

6.  Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.

Authors:  Lifeng Wang; Pengfei Zhou; Qianchi Lin; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

7.  Synthesis of benzothiophene and indole derivatives through metal-free propargyl-allene rearrangement and allyl migration.

Authors:  Jinzhong Yao; Yajie Xie; Lianpeng Zhang; Yujin Li; Hongwei Zhou
Journal:  Beilstein J Org Chem       Date:  2017-09-06       Impact factor: 2.883

  7 in total

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