An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat)
An improved lanthanum catalyst system for asymmetric amination: Toward a practical asymmetric synthesis of AS-3201 (ranirestat)
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DOI：
10.1021/ol8008446
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发表时间：
2008-07-03
期刊：
影响因子：
5.2
通讯作者：
Shibasaki, Masakatsu
中科院分区：
文献类型：
--
作者：
Mashiko, Tomoyuki;Kumagai, Naoya;Shibasaki, Masakatsu
用镧/酰胺络合物催化的不对称胺化反应得到显著改善。使用硝酸镧水合物代替三异丙氧基镧使得该方法具有可再现性、可扩展性和成本效益。La/配体/胺三元催化体系的开发是提高ee和催化转化率的关键。进行100 g规模反应，以展示AS-3201（一种高效醛糖还原酶抑制剂）关键中间体的实际合成。
A catalytic asymmetric amination with a lanthanum/amide complex was significantly improved. The use of lanthanum nitrate hydrate in place of lanthanum triisopropoxide made the process reproducible, scalable, and cost-effective. The development of a ternary catalytic system of La/ligand/amine was a key to high ee and catalytic turnover. A 100 g scale reaction was performed to showcase a practical synthesis of a key intermediate for AS-3201, a highly potent aldose reductase inhibitor.