Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes

被引：6
|
作者：
Shibata, Nina [1 ]
Tsuchiya, Takahisa [1 ]
Hashimoto, Yoshimitsu [1 ]
Morita, Nobuyoshi [1 ]
Ban, Shintaro [1 ]
Tamura, Osamu [1 ]
机构：
[1] Showa Pharmaceut Univ, 3-3165 Higashi Tamagawagakuen, Machida, Tokyo, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 14期
关键词：
HETERO-DIELS-ALDER; OXIME ETHERS; ORGANIC-SYNTHESIS; INTERMOLECULAR CYCLOADDITION; INTRAMOLECULAR CYCLOADDITION; ADDITION-CYCLIZATION; ASYMMETRIC REDUCTION; CONCISE SYNTHESIS; INDOLE ALKALOIDS; KETOXIME ETHERS;
D O I：
10.1039/c7ob00279c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
omega-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclization of the corresponding vinyl radical onto the O-silyloxime moiety to give cyclic O-silylhydroxylamines in good yields. The reactivity of O-silyloximes in radical cyclization was similar to or even higher than that of O-benzyloximes. Facile removal of the silyl group of the cyclization products leading to hydroxylamines and nitrone formation of the hydroxylamines were also demonstrated.
引用
收藏
页码：3025 / 3034
页数：10
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