Rhodium-Catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-Membered Nitrogen Heterocycles
Rhodium-Catalyzed Sequential Allylic Amination and Olefin Hydroacylation Reactions: Enantioselective Synthesis of Seven-Membered Nitrogen Heterocycles
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DOI：
10.1002/anie.201310354
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发表时间：
2014-04-01
影响因子：
16.6
通讯作者：
Nguyen, Hien M.
中科院分区：
文献类型：
--
作者：
Arnold, Jeffrey S.;Mwenda, Edward T.;Nguyen, Hien M.
本文研究了支链烯丙基乙酰亚胺酯的动态不对称胺化反应，合成了2-烷基-二氢苯并氮杂卓-5-酮。这些七元环氮杂酮是通过铑催化的烯丙基取代2-氨基芳基醛，然后通过分子内烯烃加氢酰化得到的烯醛，以良好的产率和高对映体过量制备的。这两个步骤的程序是服从不同的功能，并证明这些环系统的对映选择性制备有用。
Dynamic kinetic asymmetric amination of branched allylic acetimidates has been applied to the synthesis of 2-alkyl-dihydrobenzoazepin-5-ones. These seven-membered-ring aza ketones are prepared in good yield with high enantiomeric excess by rhodium-catalyzed allylic substitution with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step procedure is amenable to varied functionality and proves useful for the enantioselective preparation of these ring systems.