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Ag-Catalyzed difluorohydration of ß-alkynyl ketones for diastereoselective synthesis of 1,5-dicarbonyl compounds.
Zhu, Yi-Long; Wang, Ai-Fang; Du, Jian-Yu; Leng, Bo-Rong; Tu, Shu-Jiang; Wang, De-Cai; Wei, Ping; Hao, Wen-Juan; Jiang, Bo.
Afiliação
  • Zhu YL; School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn.
Chem Commun (Camb) ; 53(48): 6397-6400, 2017 Jun 13.
Article em En | MEDLINE | ID: mdl-28504286
A new catalytic difluorohydration of ß-alkynyl ketones using NFSI as the fluorinating reagent has been established, diastereoselectively furnishing a range of structurally diverse difluoride 1,5-dicarbonyl products through C(sp3)-H fluorination. Notably, the sterically encumbered t-butyl functionality located at the α-position of the carbonyl group of substrates 1 showed excellent diastereoselectivity (up to >99 : 1 dr). The reaction enabled multiple bond-forming events including two C(sp3)-F formation through Ag-catalysis to provide a highly efficient and practical method toward difluoride 1,5-dicarbonyls, some of which were successfully converted into difluorinated isoquinolines.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2017 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2017 Tipo de documento: Article