1114845-01-0Relevant academic research and scientific papers
Synthesis and use of a trifluoromethylated azomethine ylide precursor
Tran, Ga?l,Meier, Robin,Harris, Lawrence,Browne, Duncan L.,Ley, Steven V.
, p. 11071 - 11078 (2012)
The presence of fluorous substituents can impart a dramatic effect on the efficacy of molecules used for a range of applications in society. Here, we describe the preparation and use of a new trifluoromethylated azomethine ylide precursor, which leads to a series of fluorinated pyrrolidine, 3-pyrroline, and pyrrole building blocks.
Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds
Mimura, Hideyuki,Kawada, Kosuke,Yamashita, Tetsuya,Sakamoto, Takeshi,Kikugawa, Yasuo
experimental part, p. 477 - 486 (2010/05/02)
The synthesis of various trifluoromethylated amino compounds was studied using trifluoroacetaldehyde, an industrial bulk material, as a starting compound. One general application of trifluoroacetaldehyde is the preparation of trifluoroethylamino derivatives via reductive amination reaction. This synthesis includes the formation of the corresponding N,O-acetal intermediates followed by their reduction using NaBH4 or 2-picoline borane complex, affording the target trifluoroethylamino compounds in moderate to good yields (47-87%). Another general application of trifluoroacetaldehyde is the synthesis of chiral α-substituted trifluoroethylamino compounds. In this synthesis, trifluoroacetaldehyde was first converted into the chiral trifluoromethyl tert-butyl sulfinimine, which was subjected to 1,2-nucleophilic addition reactions across its C{double bond, long}N double bond. The addition of phenyllithium afforded α-(phenyl)trifluoroethylamino derivative in 83% yield and with 96% de. Allylation and Reformatsky reactions produced the corresponding α-substituted trifluoroethylamino derivatives in 82 and 58% yields and with 90 and 91% de, respectively.
