期刊
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
卷 90, 期 8, 页码 893-904出版社
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.20170086
关键词
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资金
- MEXT [15K05436]
- Grants-in-Aid for Scientific Research [26288018, 15K05436] Funding Source: KAKEN
This article describes the full details of our reductive approach to nitrones from amides. Reduction of N-siloxyamides with the Schwartz reagent [Cp2ZrHCl], followed by addition of an acid provided functionalized nitrones. The developed conditions were then extended to a catalytic version with the Vaska complex [IrCl( CO)( PPh3)(2)] and (MeHSi)(2)O starting from N-hydroxyamides. (HNMR)-H-1 studies of the Ir-catalyzed reaction revealed that the developed conditions promoted two different types of catalytic reactions including dehydrosilylation of an N-hydroxyl group and subsequent hydrosilylation of an amide carbonyl. A salient feature of our methods is their high chemoselectivity in the presence of a variety of functional groups. In addition, our reductive methods enabled concise synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods.
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