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Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement

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Published in Angewandte Chemie: International Edition. 2013, vol. 52, no. 35, p. 9266-9270
Abstract 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.
Keywords AnionsFluorineOrganocatalysisRearrangementSynthetic methods
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Other version: http://doi.wiley.com/10.1002/anie.201303527
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ROMANOV MICHAILIDIS, Fedor, GUENEE, Laure, ALEXAKIS, Alexandre. Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement. In: Angewandte Chemie: International Edition, 2013, vol. 52, n° 35, p. 9266-9270. https://archive-ouverte.unige.ch/unige:29563

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Deposited on : 2013-09-04

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