Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles.
Combining cycloisomerization with trienamine catalysis: a regiochemically flexible enantio- and diastereoselective synthesis of hexahydroindoles.
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DOI：
10.1039/c5cc08886k
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发表时间：
2016-01
影响因子：
4.9
通讯作者：
V. Chintalapudi;E. Galvin;Rebecca L. Greenaway;Edward A. Anderson
中科院分区：
文献类型：
--
作者：
V. Chintalapudi;E. Galvin;Rebecca L. Greenaway;Edward A. Anderson
本文报道了由钯催化环化异构化反应制备的吡咯烷基二烯醛经三烯胺-有机催化环加成反应合成多取代六氢吲哚。这种新型的二烯醛类的环加成进行具有优异的水平的对映体和非对映体选择性，环加成相对于栓环的区域选择性容易通过环异构化底物的设计来调整。这项工作在双立体分化三烯胺催化的第一个例子中达到高潮，其中催化剂立体控制在环加成中占主导地位，提供在每个位置特异性官能化的氮杂环产物。
The synthesis of polysubstituted hexahydroindoles through trienamine-organocatalyzed cycloadditions of pyrrolidinyl dienals, prepared by palladium-catalyzed cycloisomerization, is reported. The cycloadditions of this novel class of dienals proceed with excellent levels of enantio- and diastereoselectivity, with the regioselectivity of cycloaddition with respect to the tethering ring readily tuned through design of the cycloisomerization substrate. This work culminates in the first examples of double-stereodifferentiating trienamine catalysis, where catalyst stereocontrol dominates facial selectivity in the cycloaddition, affording azacyclic products that are specifically functionalized at every position.