Protecting group-directed annulations of tetra-substituted oxindole olefins and sulfur ylides: regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles

• Published in: RSC advances Vol. 9; no. 22; pp. 12255 - 12264
• Main Authors: Kang, Jing-Wen, Li, Xiang, Chen, Fei-Yu, Luo, Yuan, Zhang, Shu-Cang, Kang, Bin, Peng, Cheng, Tian, Xu, Han, Bo
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 17.04.2019; The Royal Society of Chemistry
• Subjects: Alkenes; Chemical reactions; Chemistry; Crystallography; Cyclopropane; Functional groups; Organic chemistry; Stereoselectivity; Substitutes; Sulfur; Synthesis
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/c9ra02192b

Protecting group-controlled annulations of tetra-substituted oxindole olefins and sulfur ylides have been achieved for the synthesis of multifunctional cyclopropane- and dihydrofuran-fused spirooxindoles. Under precise annulation regulation, a variety of cyclopropane- and dihydrofuran-fused spirooxindoles containing vicinal quaternary carbon centers were produced in up to 90% yield with up to 20 : 1 dr. This reaction demonstrates high regio-, chemo- and diastereoselectivity, broad functional group tolerance and gram-scale capacity. Protecting group-controlled regio- and chemoselective synthesis of cyclopropane- and dihydrofuran-fused spirooxindoles containing vicinal quaternary carbon centers.