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Synfacts 2013; 9(1): 0089
DOI: 10.1055/s-0032-1317735
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Pentafluorinated β-Hydroxy Ketone Synthesis via Lithium-Mediated Aldol Reaction

Contributor(s):
Paul Knochel
,
Christoph Sämann
Zhang P, Wolf C * Georgetown University, Washington, D.C., USA
Synthesis of Pentafluorinated β-Hydroxy Ketones.

J. Org. Chem. 2012;
77: 8840-8844
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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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.


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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.


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