Literature DB >> 27314605

Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans.

Carla Alamillo-Ferrer1, Marianna Karabourniotis-Sotti1, Alan R Kennedy1, Matthew Campbell2, Nicholas C O Tomkinson1.   

Abstract

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, γ-lactones, and isobenzofuranones in 44-82% yield and up to 27:1 trans selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.

Entities:  

Year:  2016        PMID： 27314605     DOI： 10.1021/acs.orglett.6b01253

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


  2 in total

1.  Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines.

Authors:  Jonathan M Shikora; Chanchamnan Um; Zainab M Khoder; Sherry R Chemler
Journal:  Chem Sci       Date:  2019-08-19       Impact factor: 9.825

2.  Alkene Syn- and Anti-Oxyamination with Malonoyl Peroxides.

Authors:  Jonathan M Curle; Marina C Perieteanu; Philip G Humphreys; Alan R Kennedy; Nicholas C O Tomkinson
Journal:  Org Lett       Date:  2020-01-30       Impact factor: 6.005
  2 in total

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