Formal (4+1) Cycloaddition and Enantioselective Michael–Henry Cascade Reactions To Synthesize Spiro[4,5]decanes and Spirooxindole Polycycles

作者：Ji‐Rong Huang, Muhammad Sohail, Tohru Taniguchi, Kenji Monde, Fujie Tanaka · 发表于：Angewandte Chemie International Edition · 年份：2017 · DOI：10.1002/anie.201701049 · 被引用次数：43 · 研究领域：Oxidative Organic Chemistry Reactions、Asymmetric Synthesis and Catalysis、Synthetic Organic Chemistry Methods

Spiro[4,5]decanes and polycyclic compounds bearing spiro[4,5]decane systems are important biofunctional molecules. Described are diastereoselective formal (4+1) cycloaddition reactions to afford oxindole-functionalized spiro[4,5]decanes and organocatalytic enantioselective Michael-Henry cascade reactions of the (4+1) cycloaddition products to generate spirooxindole polycyclic derivatives bearing the spiro[4,5]decane system. Spiro[4,5]decanes bearing oxindoles containing three stereogenic centers and spirooxindole polycycles having seven stereogenic centers, including two all-carbon chiral quaternary centers and one tetrasubstituted chiral carbon center, were obtained with high diastereo- and enantioselectivities.