【摘 要】
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Radical ipso-cyclization represented one of powerful tools towards biologically interesting spirocyclic architectures.1 Considering relatively difficult-to-controlled high reactivity of radical specie
【机 构】
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College of Biological,Chemical Science and Engineering,Jiaxing University,Jiaxing 314001
【出 处】
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中国化学会第十六届全国有机合成化学学术研讨会
论文部分内容阅读
Radical ipso-cyclization represented one of powerful tools towards biologically interesting spirocyclic architectures.1 Considering relatively difficult-to-controlled high reactivity of radical species,radical ipso-cyclization always encountered the following issues: reaction efficiency and reaction selectivity.Consequently,tremendous efforts were made on exploiting new kinds of radical ipso-cyclization reaction,which would possess high reaction efficiency and selectivity as well as an excellent reaction generality.2 In our works,we developed metal-free spiro-cyclization of N-arylpropiolamides 1 for providing a series a spirocyclic trienones 2 and 3 with high efficiency and a broad reaction scope(Fig.1).Interestingly,the N-protecting groups made a significant impact on reaction modes.Treated with bromide salt and oxone,the reaction of N-(2-oxopropyl)-N,3-diphenylpropiolamides afforded ortho-hydroxylative enones 3.The exact structure of 3 was identified with X-ray diffraction.Mechanism studies suggested that ipso cyclization-based carbonyl oxygen transfer reaction was involved in the process.Carbonyl group in product 3 was from water.
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