1354635-09-8Relevant academic research and scientific papers
Diastereoselective ritter-like reaction on cyclic trifluoromethylated N,O-acetals derived from L-tartaric acid
Jamaa, Abdelkhalek Ben,Grellepois, Fabienne
, p. 10360 - 10375 (2017)
Despite the presence of the highly electron-withdrawing fluorinated substituent, cyclic α-trifluoromethylated N-acyliminium ions were successfully generated from fluorinated O-acetyl-N,O-acetal L-tartaric acid derivatives. The addition of nitriles on these intermediates occurred with high to excellent syn diastereoselectivity and led, in most cases, to oxazolines and amides as single diastereomers. The diastereoselectivity of the addition and the nature of the reaction product depend on the substituents on the hydroxyl groups of the tartaric acid scaffold. This methodology gave access to enantiopure, highly functionalized 5-(trifluoromethyl)pyrrolidin-2-one derivatives, bearing the fluorinated substituent on a tetrasubstituted carbon.
Synthesis of novel mucic acid 1,4-lactone methyl ester 3-O-ferulate related to an extractive component isolated from the peels of Citrus sudachi
Sengoku, Tetsuya,Murata, Yusuke,Mitamura, Hiromi,Takahashi, Masaki,Yoda, Hidemi
scheme or table, p. 435 - 437 (2012/02/03)
Synthesis of a new type of mucic acid 1,4-lactone methyl ester 3-O-ferulate related to an extractive component isolated from Citrus sudachi, and its diastereomer has been achieved by employing stereodivergent dihydroxylation as a key step. The structures of the final products are fully characterized by spectroscopic methods and compared with that of the natural product.
