Premium
Reaction of 2‐(2,2,2‐Trifluoroethylidene)‐1,3‐dithiane 1‐Oxide with Ketones under Pummerer Conditions and Its Application to the Synthesis of 3‐Trifluoromethyl‐Substituted Five‐Membered Heteroarenes
Author(s) -
Kobatake Takayuki,
Yoshida Suguru,
Yorimitsu Hideki,
Oshima Koichiro
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200906774
Subject(s) - trifluoromethyl , chemistry , sigmatropic reaction , cationic polymerization , dithiane , sulfur , nucleophile , pummerer rearrangement , combinatorial chemistry , medicinal chemistry , organic chemistry , acetic anhydride , catalysis , alkyl
Easy as pie : With the aid of triflic anhydride, the title reaction resulted in nucleophilic attack of the carbonyl oxygen atom onto the activated cationic sulfur center and subsequent [3,3]‐sigmatropic rearrangement (see scheme). The products are precursors of the difficult‐to‐synthesize five‐membered 3‐trifluoromethyl heteroarene compounds.