Sophisticated utilization of oximes in construction of nitrogen-containing carbon-frameworks

2015 Fiscal Year Final Research Report

• Project/Area Number: 25460022
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Showa Pharmaceutical University
• Principal Investigator: TAMURA Osamu 昭和薬科大学, 薬学部, 教授 (30257141)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: O-シリルオキシム / N-アシルニトロン / チイルラジカル / アルキニルO-シリルオキシム / ラジカル環化 / N-ボラノニトロン / 付加環化

Outline of Final Research Achievements

(1) Omega-alkenyl oximes, on heating with Boc2O, underwent N-acylation leading to N-Boc nitrones, which caused intramolecular cycloaddition. Acylating reagent that is more adequate for the present cycloaddition was also explored. (2) A C-amide-substituted O-silylated oxime, on treatment with BF3-OEt2, in situ generated boracyclic nitrone-type intermediate, which underwent cycloaddition with alkenes to give 3,5-cis-isoxazolidines as the major products. (3) ω-Alkynyl O-tert-butyldiphenyl-　silyloximes, on treatment with odorless 4-tert-butylbenzenethiol in the presence of AIBN in boiling benzene, underwent addition of thiyl radical followed by radical cyclization of the corresponding vinyl radicals onto the O-silyloxime moieties to give cyclic O-silylhydroxylamines in good yields.

Free Research Field

有機化学