Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014, JYU, Finland.
Angew Chem Int Ed Engl. 2016 Sep 19;55(39):12104-8. doi: 10.1002/anie.201606947. Epub 2016 Sep 7.
An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).
已开发出一种不对称的有机催化串联氧化迈克尔/1,6-加成反应，用于邻羟基苯基取代的对醌亚甲和靛红衍生的烯醇酯。在 5 mol%的双功能硫脲有机催化剂存在下，这种可扩展的串联反应以良好至优异的收率（高达 98%）和非常高的立体选择性（高达>20:1 d.r.，>99%ee），提供了带有螺连接的色满骨架和三个相邻手性中心的 4-苯基取代的螺[吲哚啉-3,3'-吡咯烷]。
