Interrupting the nazarov cyclization with indoles

被引：40
作者：
Basak, Ashok K. [1 ]
Tius, Marcus A. [1 ,2 ]
机构：
[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 18期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1021/ol801587u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A carbon-terminated interrupted Nazarov reaction is described. The trimethylsilyl enol ethers derived from propargyl vinyl ketones undergo selective proton transfer at the distal acetylenic carbon atom to provide allenyl vinyl ketones as transient intermediates. In the presence of indoles, a cascade of reactions is initiated that converts the initially formed pentadienyl cations to cyclopentenones bearing a quaternary alpha carbon atom.
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收藏
页码：4073 / 4076
页数：4
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