Solvent-Minimized, Chromatography-Free, Diastereoselective Synthesis of Oxazolidine-Dispirooxindoles via oxa-1,3-Dipolar Cycloaddition of 3‑Oxindole
journal contributionposted on 06.02.2018, 00:00 authored by Peng-Ju Xia, Jun Li, Yu-Lun Qian, Qing-Lan Zhao, Hao-Yue Xiang, Jun-An Xiao, Xiao-Qing Chen, Hua Yang
An efficient and diastereoselective decarboxylative oxa-1,3-dipolar cycloaddition between 3-oxindoles and diverse amino acids is developed to access novel oxazolidine-dispirooxindole skeletons bearing vicinal quaternary carbon centers. This protocol features operational simplicity, a broad substrate scope, and good to excellent chemical yields and diastereoselectivities. In particular, minimal solvent (1 mL/10 mmol) and chromatography-free purification render this synthetic process more efficient and environmentally benign in the context of green chemistry.
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contextdiastereoselectivechromatography-free purificationOxazolidine-DispirooxindoleSolvent-MinimizedDipolar3- oxindolesDiastereoselective Synthesisacidcycloadditionvicinal quaternary carbon centerschemical yieldssubstrate scopeaccess novel oxazolidine-dispirooxindole skeletonsdiastereoselectivitieOxindoledipolardecarboxylativesimplicityprotocol featuresmLmmolChromatography-FreeCycloaddition