TY - JOUR
T1 - Domino reactions with fluorinated five-membered heterocycles - Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids
AU - Burger, Klaus
AU - Hennig, Lothar
AU - Fuchs, Annett
AU - Greif, Dieter
AU - Spengler, Jan
AU - Albericio, Fernando
PY - 2005/10
Y1 - 2005/10
N2 - A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.
AB - A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction, Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to α-trifluoromethyl-γ-ketoacids.
KW - α-Trifluoromethyl-γ-keto acids
KW - 2-Fluoro-3-trifluoromethylfurans
KW - 2-Fluoro-3-trifluoromethylthiophenes
KW - Domino reactions
KW - Trifluoromethyl substituted butenolides
UR - http://www.scopus.com/inward/record.url?scp=26244462689&partnerID=8YFLogxK
U2 - 10.1007/s00706-005-0366-z
DO - 10.1007/s00706-005-0366-z
M3 - Artículo
AN - SCOPUS:26244462689
SN - 0026-9247
VL - 136
SP - 1763
EP - 1779
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 10
ER -