TY - JOUR
T1 - New derivatives of trifluoroacetyl acetaldehyde and trifluoroaldol
AU - Kondratov, Ivan S.
AU - Gerus, Igor I.
AU - Kacharov, Aleksey D.
AU - Gorbunova, Marina G.
AU - Kukhar, Valery P.
AU - Fröhlich, Roland
PY - 2005/3
Y1 - 2005/3
N2 - 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.
AB - 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.
KW - Chiral auxiliary
KW - Fluorinated β-alkoxyvinyl ketones
KW - Fluorinated β-keto acetals
KW - O-nucleophiles
KW - Reduction
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U2 - 10.1016/j.jfluchem.2004.12.006
DO - 10.1016/j.jfluchem.2004.12.006
M3 - Article
AN - SCOPUS:15944428562
SN - 0022-1139
VL - 126
SP - 355
EP - 362
JO - Journal of Fluorine Chemistry
JF - Journal of Fluorine Chemistry
IS - 3
ER -