Regio- and stereoselective synthesis of polysubstituted 5-hydroxypyrrolidin-2-ones from 3-alkoxysuccinimides. Issue 1 (2nd January 2020)

• Record Type: Journal Article
• Authors: 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
• Is Part Of: Tetrahedron letters. Volume 61:Issue 1(2020)
• Publication Date: 2020-01-02
• Subjects: Succinimides -- Regioselective reduction -- Hydroxy-γ-lactams -- Hydroxypyrrolidinones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151358
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Regio- and stereoselective reduction protocol for the synthesis of hydroxypyrrolidin-2-ones. Regio- and stereoselective synthesis of 6-hydroxyhexahydro-4 H -furo[2, 3- c ]pyrrol-4-ones. Regio- and stereoselective reduction of 3-alkoxysuccinimides to hydroxypyrrolidin-2-ones. Abstract: The synthesis of 4-ethoxy-5-hydroxypyrrolidin-2-ones and 6-hydroxyhexahydro-4 H -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.