235418-62-9Relevant articles and documents
Diastereoselective synthesis of trans-trifluoromethyl-β-lactams and α-alkyl-β-trifluoromethyl-β-amino esters
Petrik, Vitaliy,R?schenthaler, Gerd-Volker,Cahard, Dominique
scheme or table, p. 3254 - 3259 (2011/06/11)
The diastereoselective synthesis of β-lactams was examined from N-tosyl-1-chloro-2,2,2-trifluoroethylamine 3 and various nonactivated aliphatic acid chlorides in the presence of a Br?nsted base. The mild reaction conditions allowed to get trifluoromethyl-
Synthesis of organofluorine compounds using the ene reaction of N-(p- toluenesulfonyl)trifluoroacetaldehyde imine
Jonoshita, Shuichi,Harada, Atsuhiro,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 656 - 662 (2007/10/03)
N-Tosyltrifluoroacetaldehyde imine (4) reacted with terminal olefins by only heating together to give the ene reaction products. This means the imine is much more reactive than trifluoroacetaldehyde (2) itself as an enophile. However, 4 was very sensitive to moisture and the yields were low even if it was used without isolation. Further, it did not react with non-terminal olefins. In the course on study of the mechanism of this reaction, we found that N-(2,2,2-trifluoro-1-ethoxyethyl)tosylamide (12), obtained by the reaction of trifluoroacetaldehyde ethyl hemiacetal (1) with tosylamide (3) in the presence of titanium(IV) chloride followed by addition of ethanol, reacted in the presence of sodium hydride and titanium(IV) chloride to give the same products from the ene reaction of 4 in much better yields. Interestingly, this reaction proceeded with non-terminal olefins.