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Fedor Romanov-Michailidis, Dr. Laure Guénée and Prof. Dr. Alexandre Alexakis Enantioselective Organocatalytic Fluorination-Induced Wagner–Meerwein Rearrangement Angewandte Chemie International Edition 52

Article first published online: 14 JUL 2013 | DOI: 10.1002/anie.201303527

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Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group.

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