A Two-Step, Formal [4+2] Approach toward Piperidin-4-ones via Au Catalysis

被引：160
|
作者：
Cui, Li [1 ]
Peng, Yu [1 ]
Zhang, Liming [1 ]
机构：
[1] Univ Nevada, Dept Chem 216, Reno, NV 89557 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 24期
基金：
美国国家科学基金会;
关键词：
GOLD CATALYSIS; TRANSFORMATIONS; HETEROCYCLES; ACTIVATION; GENERATION; INSERTION; PLATINUM; BONDS;
D O I：
10.1021/ja903531g
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines; in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstrated in a highly diastereoselective synthesis of (+/-)-cermizine C.
引用
收藏
页码：8394 / +
页数：3
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