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Synthesis and Applications of 3‐Methylene‐4‐(trifluoromethyl)azetidin‐2‐ones as Building Blocks for the Preparation of Mono‐ and Spirocyclic 4‐CF 3 ‐β‐Lactams
Author(s) -
Dao Thi Hang,
Danneels Barbara,
Desmet Tom,
Van Hecke Kristof,
Van Nguyen Tuyen,
D'hooghe Matthias
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600387
Subject(s) - chemistry , trifluoromethyl , methylene , electrophile , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , alkyl
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‐CF 3 ‐β‐lactams as useful synthetic intermediates en route to a variety of biologically relevant CF 3 ‐functionalized target structures.