RCM-mediated synthesis of trifluoromethyl-containing nitrogen heterocycles.
A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.
De Matteis
Valeria
V
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.
van Delft
Floris L
FL
Jakobi
Harald
H
Lindell
Stephen
S
Tiebes
Jörg
J
Rutjes
Floris P J T
FP
D005617:Chlorofluorocarbons, Methane; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D009584:Nitrogen; D010880:Piperidines / Q000138:chemical synthesis*
D005617:Chlorofluorocarbons, Methane; D006571:Heterocyclic Compounds; D010880:Piperidines; D009584:Nitrogen; C009554:fluoroform