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Stereoselective Ring‐Opening of gem ‐Difluorocyclopropanes: An Entry to Stereo‐defined ( E , E )‐ and ( E , Z )‐Conjugated Fluorodienes
Author(s) -
Specklin Simon,
Fenneteau Johan,
Subramanian Parthasarathi,
Cossy Janine
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704956
Subject(s) - conjugated system , ring (chemistry) , stereoselectivity , selectivity , yield (engineering) , chemistry , stereochemistry , organic chemistry , physics , catalysis , polymer , thermodynamics
The ring‐opening of gem ‐difluorocyclopropyl acetaldehydes producing selectively ( E , E )‐ and ( E , Z )‐conjugated fluorodienals is described. Two stereo‐divergent methods are presented to access both stereoisomers from a common precursor, in high yield and selectivity. The mechanistic aspect of these transformations is discussed.