Stereoselective amination of 5-substituted γ-lactones and γ-lactams - A convenient route for the preparation of 5-substituted (3S,5S)-3- acetylaminotetrahydrofuran-2-ones and (3S,5S)-3-acetylaminopyrrolidin-2-ones

Article abstract of DOI:10.1002/(SICI)1099-0690(199907)1999:7<1581::AID-EJOC1581>3.0.CO;2-2

5-Substituted (S)-tetrahydrofuran-2-ones (1a,b) and (S)pyrrolidin-2- ones (1c,d) were transformed in three steps, by treatment with tert- butoxybis(dimethylamino)methane (Bredereck's reagent), followed by nitrosation and stereoselective catalytic hydrogenation, into the corresponding 5-substituted (3S,5S)-3-acetylaminotetrahydrofuran-2-ones (4a,b) and (3S,5S)-3-acetylaminopyrrolidin-2-ones (4c,d).