On the Gold-Catalyzed Intramolecular 7-exo-trig Hydroamination of Allenes

被引：34
|
作者：
Pflaesterer, Daniel [1 ]
Dolbundalchok, Praphasiri [1 ]
Rafique, Shahid [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Hashmi, A. Stephen K. [1 ]
机构：
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2013年 / 355卷 / 07期
关键词：
alkenes; allenes; benzoxazepines; gold; hydroamination; GOLD(I)-CATALYZED ENANTIOSELECTIVE HYDROAMINATION; INTERMOLECULAR HYDROAMINATION; REVERSE-TRANSCRIPTASE; EFFICIENT SYNTHESIS; ALPHA-AMINOALLENES; HIV-1; REPLICATION; POTENT; CYCLOISOMERIZATION; CYCLIZATION; DISCOVERY;
D O I：
10.1002/adsc.201300154
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Aniline derivatives with allene side tethers were tested as substrates for a gold-catalyzed 7-exo-trig hydroamination reaction. The nucleophilicity of the aniline derivatives plays an important role for the outcome of the reaction. While electron-deficient protecting groups at the nitrogen led to competing pathways like hydroarylation or an allene to diene isomerization, clean formation of the desired benzoxazepines was obtained with unprotected aniline derivatives.
引用
收藏
页码：1383 / 1393
页数：11
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