Zhang P, Wolf C * Georgetown University, Washington, D.C., USA
Synthesis of Pentafluorinated β-Hydroxy Ketones.
J. Org. Chem. 2012;
77: 8840-8844
Key words
pentafluorinated β-hydroxy ketones - aldol reaction - lithium
Significance
A fast and mild synthesis of pentafluorinated β-hydroxy ketones has been disclosed.
The reaction proceeds via a lithium-promoted aldol reaction of readily available
difluoroenolate precursors with trifluoromethyl ketones furnishing the corresponding
pentafluorinated β-hydroxy ketones in good to excellent yield.
Comment
The described reaction is very versatile since it proceeds under ambient temperature
and tolerates a broad range of functional groups. Furthermore, the authors show that
the reduction of the pentafluorinated β-hydroxy ketones furnishes quantitatively
the corresponding 1,3-diols favoring the syn-isomer.
