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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

✍ Scribed by Marko S'kof; Jurĳ Svete; Matej Kmetič; Simona Golič-Grdadolnik; Branko Stanovnik

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 249 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199907)1999:7<1581::aid-ejoc1581>3.0.co;2-2

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✦ Synopsis

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

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