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Scientific article
English

Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement

Published inAngewandte Chemie, vol. 52, no. 35, p. 9266-9270
Publication date2013
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
  • Anions
  • Fluorine
  • Organocatalysis
  • Rearrangement
  • Synthetic methods
Citation (ISO format)
ROMANOV MICHAILIDIS, Fedor, GUENEE, Laure, ALEXAKIS, Alexandre. Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement. In: Angewandte Chemie, 2013, vol. 52, n° 35, p. 9266–9270. doi: 10.1002/anie.201303527
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ISSN of the journal1433-7851
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Creation09/02/2013 4:55:00 PM
First validation09/02/2013 4:55:00 PM
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