Journal of Organic Chemistry p. 4639 - 4642 (1990)
Update date:2022-08-04
Topics:
Thenappan, Alagappan
Burton, Donald J.
A reduction-olefination sequence has been used to convert esters to α-fluoro α,β-unsaturated esters.In the presence of diisobutylaluminum hydride, esters are reduced to aldehydes that react in situ with <(EtO)2P(O)CFC(O)Et>-Li+ to form the title compounds in good yield with high stereoselectivity.The reaction is applicable to aliphatic, aromatic, cyclic, unsaturated, perfluorinated, and partially fluorinated esters.The E/Z ratio of unsaturated esters formed in the reaction varies with the cations present in the reaction mixture.Solvents have very little influence on stereochemistry.The sequential transformation of PhC(O)OBun to (E)-PhCH=CFC(O)OEt and then to (E,E)-PhCH=CFCH=CFC(O)OEt illustrates the scope of this methodology, which introduces a fluorine atom adjacent to an ester functionality with concomitant elongation of the chain by two carbon atoms.
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