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Regio- and stereoselective synthesis of polysubstituted 5-hydroxypyrrolidin-2-ones from 3-alkoxysuccinimides

Author:
da Silva, Fabio M., da Silva, Andreia M.P.W., Mittersteiner, Mateus, Andrade, Valquiria P., da C. Aquino, Estefania, Bonacorso, Helio G., Martins, Marcos A.P., Zanatta, Nilo
Source:
Tetrahedron letters 2019
ISSN:
0040-4039
Subject:
chemical reactions, chemical structure, organic compounds, sodium borohydride, stereoselective synthesis, stereoselectivity, temperature
Abstract:
The synthesis of 4-ethoxy-5-hydroxypyrrolidin-2-ones and 6-hydroxyhexahydro-4H-furo[2,3-c]pyrrol-4-ones — through the regio- and stereoselective reduction of the corresponding 3-alkoxysuccinimides — is described. The reaction used NaBH4 at low temperatures and short reaction times, providing products with yields of up to 77%. The stereoselectivity was highly influenced by both alkoxy and the N-moiety in the starting succinimide.
Agid:
6754618