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Stereoselective Amination of 5‐Substituted γ‐Lactones and γ‐Lactams – A Convenient Route for the Preparation of 5‐Substituted (3 S ,5 S )‐3‐Acetylaminotetrahydrofuran‐2‐ones and (3 S ,5 S )‐3‐Acetylaminopyrrolidin‐2‐ones
Author(s) -
S'kof Marko,
Svete Jurij,
Kmetič Matej,
GoličGrdadolnik Simona,
Stanovnik Branko
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199907)1999:7<1581::aid-ejoc1581>3.0.co;2-2
Subject(s) - chemistry , stereoselectivity , tetrahydrofuran , amination , reagent , catalysis , stereochemistry , organic chemistry , medicinal chemistry , solvent
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 (3 S ,5 S )‐3‐acetylaminotetrahydrofuran‐2‐ones ( 4a , b ) and (3 S ,5 S )‐3‐acetylaminopyrrolidin‐2‐ones ( 4c , d ).