Literature DB >> 19627130

Practical synthesis and highly diastereoselective Diels-Alder reactions of 1-alkylthio-3-silyloxybutadienes.

Janice M Holmes1, Andrea L Albert, Michel Gravel.   

Abstract

An efficient acid-catalyzed method for the synthesis of vinylogous thioesters was developed. 1-Alkylthio-3-silyloxybutadienes were then produced in high yields from the corresponding vinylogous thioesters. These dienes were highly reactive in Diels-Alder reactions, affording the cycloadducts in high endo selectivity under mild conditions.

Entities:  

Year:  2009        PMID: 19627130     DOI: 10.1021/jo901347u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Visible light mediated metal-free thiol-yne click reaction.

Authors:  Sergey S Zalesskiy; Nikita S Shlapakov; Valentine P Ananikov
Journal:  Chem Sci       Date:  2016-07-12       Impact factor: 9.825

2.  Intermolecular Photocatalytic Chemo-, Stereo- and Regioselective Thiol-Yne-Ene Coupling Reaction.

Authors:  Julia V Burykina; Andrey D Kobelev; Nikita S Shlapakov; Alexander Yu Kostyukovich; Artem N Fakhrutdinov; Burkhard König; Valentine P Ananikov
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-02       Impact factor: 16.823

  2 in total

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