New derivatives of trifluoroacetyl acetaldehyde and trifluoroaldol |
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Authors: | Ivan S Kondratov Aleksey D Kacharov Valery P Kukhar |
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Institution: | a Institute of Bioorganic Chemistry and Petrochemistry of National Ukrainian Academy of Science, Murmanska 1, Kiev 02094, Ukraine b Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany |
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Abstract: | The reaction of β-ethoxyvinyl trifluoromethyl ketone 1 with O-nucleophiles such as alcohols and diols leads to various derivatives of trifluoroacetyl acetaldehyde, such as β-alkoxyvinyl trifluoromethyl ketones 3 and cyclic keto acetals 4. Several derivatives synthesized contain chiral auxiliaries. Reduction of the compounds 1, 3, 4 under various reaction conditions leads to the trifluoroaldol derivatives 6, 7, 9, 10 containing a protected aldehyde group. The compounds obtained are useful building blocks in fluoroorganic synthesis. |
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Keywords: | Fluorinated β-alkoxyvinyl ketones Fluorinated β-keto acetals O-nucleophiles Chiral auxiliary Reduction |
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