Synthesis and Applications of 3-Methylene-4-(trifluoromethyl)azetidin-2-ones as Building Blocks for the Preparation of Mono- and Spirocyclic 4-CF3-β-Lactams

• Published in: Asian journal of organic chemistry Vol. 5; no. 12; pp. 1480 - 1491
• Main Authors: Dao Thi, Hang, Danneels, Barbara, Desmet, Tom, Van Hecke, Kristof, Van Nguyen, Tuyen, D'hooghe, Matthias
• Format: Journal Article
• Language: English
• Published: Blackwell Publishing Ltd 01-12-2016
• Subjects: 3-methylene-4-(trifluoromethyl)azetidin-2-ones; cycloadditions; electrophilic additions; fluorinated compounds; Michael addition; spirocyclic lactams
• ISSN: 2193-5807; 2193-5815
• DOI: 10.1002/ajoc.201600387

3‐Methylene‐4‐(trifluoromethyl)azetidin‐2‐ones were efficiently prepared from the corresponding 3‐oxo‐4‐trifluoromethyl‐β‐lactams and successfully evaluated as novel building blocks in organic synthesis. In particular, Michael additions, electrophilic additions, and cycloadditions were applied to allow easy access to a broad variety of stereodefined mono‐ and spirocyclic 4‐CF3‐β‐lactams as useful synthetic intermediates en route to a variety of biologically relevant CF3‐functionalized target structures.
3‐Methylene‐4‐(trifluoromethyl)azetidin‐2‐ones were efficiently prepared from the corresponding 3‐oxo‐4‐trifluoromethyl‐β‐lactams. Michael additions, electrophilic additions, and cycloadditions were applied to allow easy access to a broad variety of stereodefined mono‐ and spirocyclic 4‐CF3‐β‐lactams as useful synthetic intermediates en route to a variety of biologically relevant CF3‐functionalized target structures.