282102-35-6Relevant academic research and scientific papers
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.
Mannich-Type Reaction with Trifluoromethylated N,O-Hemiacetal: Facile Preparation of β-Amino-β-trifluoromethyl Carbonyl Compounds
Takaya, Jun,Kagoshima, Hirotaka,Akiyama, Takahiko
, p. 1577 - 1579 (2007/10/03)
(Matrix Presented) On treatment of silyl enolates and an N,O-hemiacetal, derived from trifluoroacetaldehyde ethyl hemiacetal and p-anisidine, with GaCl3 (0.2 equiv) and C6H5COCl (0.2 equiv) in propionitrile, Mannich-type r
