Diethylzinc-mediated one-step stereoselective synthesis of alpha-fluoroacrylates from aldehydes and ketones. Two different pathways depending on the carbonyl partner.
A efficient methodology allowing the one-pot stereoselective synthesis of alpha-fluoroacrylates, based on the addition of ethyl dibromofluoroacetate to a carbonyl derivative using diethylzinc as organometallic mediator, is described. Two different pathways have been identified depending on the involved carbonyl partner. In the case of aldehydes, an E2-type mechanism has been identified, whereas ketones go through an E1cb-type mechanism.
Lemonnier
G
G
INSA de Rouen et Université de Rouen, CNRS UMR 6014 C.O.B.R.A & FR 3038, IRCOF, 76821 Mont-Saint-Aignan Cedex, France.
Zoute
L
L
Dupas
G
G
Quirion
J-C
JC
Jubault
P
P
D000179:Acrylates / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D054879:Halogenation; D007659:Ketones / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D009942:Organometallic Compounds; D013237:Stereoisomerism
D000179:Acrylates; D000447:Aldehydes; D007659:Ketones; D009942:Organometallic Compounds; C454811:diethylzinc