含三氟甲基手性毗邻双螺环氧化吲哚的合成

Synthesis of Trifluoromethyl-containing Dispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters

以10 mol%β-ICD作催化剂,靛红衍生的MBH-碳酸酯与3-(2,2,2-三氟次乙基)氧化吲哚为原料,经不对称[3+2]环加成反应,合成了10个含三氟甲基的手性毗邻双螺环氧化吲哚类化合物(3a^3j),收率68%~98%,dr值97/3~>99/1,ee值96%~>99%,其结构经^1H NMR,^13C NMR确证。

A β-ICD catalyzed asymmetric [3+2] cycloaddition reaction of isatin-derived MBH carbonates with 3-(2,2,2-trifluoroethyl)ideneoxindoles was realized. Ten trifluoromethyl-containing 3,3’-cyclopentenyldispirooxindoles(3a^3j)incorporating two adjacent quaternary spirostereocenters were obtained with yields of 68%~98%, dr 97/3~>99/1 and ee 96%~>99%. The structures were confirmed by ^1H NMR and ^13C NMR.