Consecutive Aminolithiation-Carbolithiation of Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety Giving Hydroindolizine
Consecutive Aminolithiation-Carbolithiation of Linear Aminoalkene Bearing Terminal Vinyl Sulfide Moiety Giving Hydroindolizine
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带有末端乙烯基硫部分的线性氨基烯烃的连续氨基锂化-碳锂化得到氢吲哚嗪
DOI：
10.1055/s-0036-1588522
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发表时间：
2017
期刊：
影响因子：
2
通讯作者：
Kiyoshi Tomioka
中科院分区：
文献类型：
--
作者：
Yasutomo Yamamoto;Tatsuya Yamaguchi;Atsunori Kaneshige;Aiko Hashimoto;Sachiho Kaibe;Akari Miyawaki;Ken-ichi Yamada;Kiyoshi Tomioka
使用化学计量的BuLi，带有乙烯基硫醚部分的氨基烯烃的氨基锂化-碳锂化串联环化顺利进行。在室温下，氨基锂化和碳锂化反应均处于平衡状态，环化反应的立体化学受手性控制。在-78 °C下，该反应是动力学控制的，并且环化产物1，2-二取代八氢中氮茚以良好的非对映选择性获得。
Aminolithiation–carbolithiation tandem cyclization of an aminoalkene bearing vinyl sulfide moiety proceeded smoothly using stoichiometric amounts of BuLi. Both aminolithiation and carbolithiation were in equilibrium at room temperature, and the stereochemistry of the cyclization was thermodynamically controlled. At –78 °C the reaction was kinetically controlled and the cyclized product, 1,2-disubstituted octahydroindolizine, was obtained with good diastereoselectivity.