Diastereoselective [3 + 1] Cyclization Reaction of Oxindolyl Azaoxyallyl Cations with Sulfur Ylides: Assembly of 3,3′-Spiro[β-lactam]-oxindoles
Hai‐Jun Leng, Qing‐Zhu Li, Peng Xiang, Ting Qi, Qing‐Song Dai, Zhi-Qiang Jia, Chuan Gou, Xiang Zhang, Jun‐Long Li
Abstract
Oxindoles and β-lactams are attractive structural motifs because of their unique biological importance. However, the fusion of the two moieties featuring 3,3'-spirocyclic scaffolds is a challenging task in organic synthesis. Herein we designed a novel type of oxindole-based azaoxyallyl cation synthons, which could readily participate in the [3 + 1] cyclization with sulfur ylides. With this protocol, a collection of 3,3-spiro[β-lactam]-oxindoles were facilely produced in up to 94% yield with perfect diastereoselectivity.
Topics & Concepts
ChemistrySulfurLactamBeta-lactamStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryAntibioticsBiochemistrySynthesis and Biological EvaluationSynthesis and Reactions of Organic CompoundsStructural and Chemical Analysis of Organic and Inorganic Compounds