4.5 Article

Sequential Acylation/Silylation/Hetero-Claisen Rearrangement of Nitroalkanes for the Synthesis of Protected Hydroxyoxime Derivatives

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2021, 期 22, 页码 3197-3213

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100469

关键词

Acylation; Nitro compounds; Oxygenation; Protecting groups; Rearrangement

资金

  1. Russian Science Foundation [20-13-18013] Funding Source: Russian Science Foundation

向作者/读者索取更多资源

Sequential acylation-silylation of nitroalkanes leads to high yields of O-silylated alpha-acyloxyoximes. The reaction has a broad substrate scope for both nitroalkanes and acylating agents, with the ability to adjust reaction conditions based on the specific substrate. Additionally, the study demonstrates the application of the obtained oxime derivatives in organic synthesis.
Sequential acylation-silylation of nitroalkanes leads to O-silylated alpha-acyloxyoximes in high yields. The first step of the reaction involves deprotonation of nitro compound with sodium hydride promoted by DBU or alcohol/15-crown-5 system followed by treatment with acyl chloride. In situ generated acyl nitronate is further silylated by silyl triflate that triggers hetero-Claisen [3,3]-rearrangement within N-acyloxyenamine moiety furnishing orthogonally protected oxime derivatives. The procedure has large substrate scope for both nitroalkanes and acylating agents (acyl chlorides, chloroformates) and allows tuning of reaction conditions depending on the particular type of substrate. Application of obtained oxime derivatives in organic synthesis is demonstrated.

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