Radical Cyclization in Heterocycle Synthesis 15 : Relationship between a Radical Species and Radical Acceptors of Three Different Types of Double Bond in Radical Addition-Cyclization
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概要
- 論文の詳細を見る
Relationship between a radical species and radical acceptors of three different types of double bond in radical addition-cyclization was systematically investigated. Substrates carrying α, β-unsaturated amide, isolated olefin, and oxime ether moieties underwent radical addition-cyclization to give differently substituted lactams depending upon the radicals used. The sulfanyl radical addition-cyclization of the substrate proceeded smoothly to give the 5-membered lactam having an alkoxyamino group as a result of preferable addition of an intermediary α-carbonyl radical to the oxime ether. On the other hand, the triethylborane-mediated radical addition-cyclization gave the lactam bearing an iodomethyl group as a result of addition to an intermediary α-carbonyl radical to isolated olefin. The different regioselectivity was explained by the stability of the intermediary radical and the interaction between SOMO and HOMO.
- 公益社団法人日本薬学会の論文
- 2005-08-01
著者
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NAITO Takeaki
Kobe Pharmaceutical University
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Naito Takeaki
Kobe Pharmaceutical Univ.
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MIYATA Okiko
Kobe Pharmaceutical University
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Ueda Masafumi
Kobe Pharmaceutical University
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KAJISA Seiko
Kobe Pharmaceutical University, Motoyamakita
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YAMAUCHI Masashige
Department of Pharmaceutical Sciences, Josai University
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Kajisa Seiko
Kobe Pharmaceutical University Motoyamakita
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Yamauchi Masashige
Department Of Pharmaceutical Sciences Josai University
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Miyata Okiko
Kobe Pharmaceutical Univ.
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Kajisa Seiko
Kobe Pharmaceutical University
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