Access to Benzylic Quaternary Carbons from Aromatic Ketones

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 t...

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Veröffentlicht in:Organic letters 2019-08, Vol.21 (15), p.6050-6053
Hauptverfasser: Li, You, Han, Jingpeng, Luo, Han, An, Qiaoyu, Cao, Xiao-Ping, Li, Baosheng
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02204