Modified Julia fluoroolefination: selective preparation of fluoroalkenoates.
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.
Pfund
Emmanuel
E
Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen Basse-Normandie, CNRS, 6 boulevard du Maréchal Juin, 14050 Caen, France.
Lebargy
Cyril
C
Rouden
Jacques
J
Lequeux
Thierry
T
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D052160:Benzothiazoles / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D000447:Aldehydes; D000475:Alkenes; D052160:Benzothiazoles; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D013450:Sulfones