Catalytic Carbon-Carbon Bond-Forming Reactions of Aminoalkane Derivatives with Imines
Catalytic Carbon-Carbon Bond-Forming Reactions of Aminoalkane Derivatives with Imines
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DOI：
10.1021/ja909909q
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发表时间：
2010-03-17
影响因子：
15
通讯作者：
Kobayashi, Shu
中科院分区：
文献类型：
--
作者：
Chen, Yi-Jing;Seki, Kazutaka;Kobayashi, Shu
以9-亚芴基为氮原子的保护和活化基团，成功地催化了氨基烷烃与亚胺的C-C键形成反应。使用（KOBU）-Bu-t/18-冠-6或2，6-二甲基苯酚钾作为催化剂，以高收率和高非对映选择性获得所需产物。广泛的底物范围，包括简单的氨基烷烃和各种亚胺，已被证明。对于所获得的产物，在酸性条件下选择性脱保护是可能的，以高产率得到所需的单胺和二胺衍生物，并定量回收9-芴酮。催化不对称变体的初步研究表明，在所需的产品有希望的对映选择性。
Catalytic C C bond-forming reactions of aminoalkanes with imines were successfully performed using 9-fluorenylidene as a protecting and activating group of the nitrogen atom. The desired products were obtained in high yields with high diastereoselectivities using (KOBu)-Bu-t/18-crown-6 or potassium 2,6-dimethylphenoxide as a catalyst. A wide substrate scope, including simple aminoalkanes and a variety of imines, has been demonstrated. For the products obtained, selective deprotection was possible under acidic conditions to give the desired monoamine and diamine derivatives in high yields with quantitative recovery of 9-fluorenone. A preliminary study of a catalytic asymmetric variant showed promising enantioselectivity in the desired product.