A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.
A stereocontrolled synthesis of (±)-xenovenine via a scandium(III)-catalyzed internal aminodiene bicyclization terminated by a 2-(5-ethyl-2-thienyl)ethenyl group.
复制标题
通过钪(III)催化的内部氨基二烯双环化（以2-(5-乙基-2-噻吩基)乙烯基封端）立体控制合成(±)-xenovenine。
DOI：
10.1021/ol101646t
复制
发表时间：
2010
期刊：
影响因子：
5.2
通讯作者：
Livinghouse,Tom
中科院分区：
文献类型：
--
作者：
Jiang,Tao;Livinghouse,Tom
含有 2-(5-乙基-2-噻吩基)乙烯基终止剂的 5-氨基-1,8-二烯的高度非对映选择性二元氢胺化已用于有效合成 (±)-xenovenine (1)。与简单的 1,2-二取代烯烃相比，观察到 2-（杂芳族）乙烯基的环化速率显着提高。
A highly diastereoselective binary hydroamination of a 5-amino-1,8-diene containing a 2-(5-ethyl-2-thienyl)ethenyl terminator has been utilized in an efficient synthesis of (±)-xenovenine (1). A pronounced rate enhancement was observed for cyclization onto the 2-(heteroaromatic)ethenyl group in comparison to a simple 1,2-disubstituted alkene.