Modified Julia fluoroolefination: selective preparation of fluoroalkenoates |
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| Authors: | Pfund Emmanuel Lebargy Cyril Rouden Jacques Lequeux Thierry |
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| Institution: | Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 boulevard du Maréchal Juin, 14050 Caen, France. |
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| Abstract: | The modified Julia olefination reaction has been applied to develop a stereoselective synthesis of fluoroalkenoate derivatives from a fluorobenzothiazolyl sulfone and aldehydes or a ketone. The olefination reaction can be achieved by using a variety of bases. DBU and DBU in the presence of MgBr2 were found to be the most efficient systems to prepare either (Z)- or (E)-alkenoates in moderate to excellent stereoselectivity. |
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