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

页码：3025 / 3034

页数：10

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