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