Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
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DOI：
10.1021/jo902540x
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发表时间：
2010-01
期刊：
影响因子：
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通讯作者：
Masafumi Ueda;S. Kawai;Masataka Hayashi;T. Naito*;O. Miyata
中科院分区：
文献类型：
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作者：
Masafumi Ueda;S. Kawai;Masataka Hayashi;T. Naito*;O. Miyata
通过N-茚满基（甲氧基）胺的多米诺反应，实现了2-取代四氢喹啉类化合物的高效合成。该反应包括三种类型的反应：醇的消除反应、芳基的重排反应和有机锂或镁试剂的加成反应。该方法的合成效用通过立体选择性地合成（+/-）- martinellic酸来证明。
A new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (+/-)- martinellic acid.