Friedel-Crafts Reaction of Indoles with Isatin-Derived β,γ-Unsaturated α-Keto Esters Using a BINOL-Derived Bisoxazoline (BOX)/Copper(II) Complex as Catalyst
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- 作者：Nai-Kai Li ; Ling-Pei Kong ; Zheng-Hang Qi ; Shao-Jie Yin ; Jun-Qi Zhang ; Bing Wu and Xing-Wang Wang
- 刊名：Advanced Synthesis & Catalysis
- 出版年：2016
- 出版时间：October 6, 2016
- 年：2016
- 卷：358
- 期：19
- 页码：3100-3112
- 全文大小：881K
- ISSN：1615-4169
文摘
Several chiral BINOL-derived bisoxazoline (BOX)/copper(II) complexes were synthesized and evaluated as catalysts for the Friedel–Crafts reaction of indoles with isatin-derived β,γ-unsaturated α-keto esters. The resulting bis-indole products bearing a quaternary stereocenter were obtained in excellent yields and enantioselectivities. Additionally, the desired products were practically transformed to α-amino esters, α-hydroxy esters and α-keto amides. It is noteworthy that this catalytic procedure was conducted with a catalyst loading of 0.5 mol% without any discernible decrease in the reactivity or enantioselectivity.