Literature DB >> 31310556

Access to Benzylic Quaternary Carbons from Aromatic Ketones.

You Li1, Jingpeng Han2, Han Luo2, Qiaoyu An2, Xiao-Ping Cao1, Baosheng Li1,2.   

Abstract

The construction of benzylic all-carbon quaternary stereocenters, which are ubiquitous in biomolecules and drugs, is a task of high practical significance. Herein, we disclose a highly efficient one-pot method of constructing all-carbon quaternary structural units from aryl ketones, revealing that the entire process involves three consecutive chemical events, namely nucleophilic addition, Meinwald 1,2-hydrogen migration, and alkylation. Interestingly, dimerization of acetophenones results in formation of 2,4-diarylfurans under the employed conditions rather than the quaternary carbon products.

Entities:  

Year:  2019        PMID: 31310556     DOI: 10.1021/acs.orglett.9b02204

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


  2 in total

Review 1.  Synthetic Access to Aromatic α-Haloketones.

Authors:  Marre Porré; Gianmarco Pisanò; Fady Nahra; Catherine S J Cazin
Journal:  Molecules       Date:  2022-06-02       Impact factor: 4.927

2.  Regioselective molybdenum-catalyzed allylic substitution of tertiary allylic electrophiles: methodology development and applications.

Authors:  Muhammad Salman; Yaoyao Xu; Shahid Khan; Junjie Zhang; Ajmal Khan
Journal:  Chem Sci       Date:  2020-05-06       Impact factor: 9.825

  2 in total

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