Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene.
J Org Chem, 2018/05/18;83(10):5392-5397.
Dobrynin SA[1, 2], Glazachev YI[3], Gatilov YV[1], Chernyak EI[1], Salnikov GE[1, 2], Kirilyuk IA[1, 2]
Affiliations
PMID: 29668276DOI: 10.1021/acs.joc.8b00085
Impact factor: 4.198
Abstract
A simple method for the synthesis of sterically shielded pyrrolidine nitroxides, including the title compound, has been suggested. The key procedure implies assembling the pyrrolidine ring from α-amino acid, ketone, and activated alkene in a three-component domino process, followed by oxidation to nitrone and Grignard reagent addition. The new nitroxides demonstrate very high stability against reduction with ascorbate.
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