Highly Efficient Enantioselective Construction of Bispirooxindoles Containing Three Stereocenters through an Organocatalytic Cascade Michael-Cyclization Reaction
作者:Hao Wu、Li-Li Zhang、Zhi-Qing Tian、Yao-Dong Huang、Yong-Mei Wang
DOI:10.1002/chem.201203221
日期:2013.1.28
Bispirooxindole derivatives containing three stereocenters, including two spiro quaternary centers, were synthesized in a high‐yielding, atypically rapid, and stereocontrolled cascade Michael–cyclization reaction between methyleneindolinones and isothiocyanato oxindoles catalyzed by a bi‐ or multifunctional organocatalyst. Mild conditions were used to construct bispirooxindoles with excellent enantio‐
在一个高产,非典型快速且立体控制的双-或多功能有机催化剂催化的亚甲基吲哚酮与异硫氰酸根合吲哚之间的级联迈克尔-环化反应中,合成了包含三个立体中心(包括两个螺环季铵中心)的双螺并恶唑衍生物。温和的条件用于在不到1分钟的时间内构建具有优异对映异构体和非对映异构体纯度的bispirooxindoles。催化剂的重新配置提供了进入相反对映异构体的途径。这种异常高效的方法将使具有潜在生物活性的这一类有趣的化合物的面向多样性的合成成为可能。