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Abstract
After optimization for catalyst stability, 4-chlorobenzoic acid emerged as the optimal catalyst for the aliphatic ketone Claisen rearrangement. The protocol enables a one-pot, metal-free, catalytic protocol from allylic alcohols to γ,δ-unsaturated ketones. The optimized process tolerates a range of substrates, including substituents with acid-labile protecting groups. Reaction monitoring and DFT studies of the aliphatic ketone Claisen process agree that the ultimate rearrangement step typically has the highest activation barrier.
Supplementary materials
Title
Experimental and computational details
Description
Experimental procedures, optimization and same excess experiments, characterization data, and computational details
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Title
Cartesian coordinates
Description
XYZ coordinates of computed structures (ZIP)
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Title
NMR FAIRDATA
Description
FAIR data, including the primary NMR FID files, for compounds 1b-1z, S1a-S1c, 6a-6aa, S6a-S6c, 4a, 4p, 5a, 5p (ZIP)
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Title
NMR spectra and GC chromatograms
Description
Copies of NMR spectra and GC chromatograms (PDF)
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