Literature DB >> 23343463

Rapid and stereoselective synthesis of spirocyclic ethers via the intramolecular Piancatelli rearrangement.

Leoni I Palmer1, Javier Read de Alaniz.   

Abstract

The first example of a Piancatelli rearrangement of alcohols is demonstrated utilizing dysprosium(III) triflate as a catalyst to access oxaspirocycles in a highly diastereoselective manner. The cascade reaction constructs the spirocyclic ether ring system and the tertiary stereocenter in a single operation and is experimentally easy to perform.

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Year:  2013        PMID： 23343463     DOI： 10.1021/ol303263q

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  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

2.  Automatic mapping of atoms across both simple and complex chemical reactions.

Authors:  Wojciech Jaworski; Sara Szymkuć; Barbara Mikulak-Klucznik; Krzysztof Piecuch; Tomasz Klucznik; Michał Kaźmierowski; Jan Rydzewski; Anna Gambin; Bartosz A Grzybowski
Journal:  Nat Commun       Date:  2019-03-29       Impact factor: 14.919

3.  Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement.

Authors:  Gabrielle R Hammersley; Meghan F Nichol; Helena C Steffens; Jose M Delgado; Gesine K Veits; Javier Read de Alaniz
Journal:  Beilstein J Org Chem       Date:  2019-07-12       Impact factor: 2.883
  3 in total

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