167282-09-9Relevant articles and documents
Synthesis of enantiopure trifluoromethyl building blocks via a highly chemo- and diastereoselective nucleophilic trifluoromethylation of tartaric acid-derived diketones
Massicot, Fabien,Monnier-Benoit, Nicolas,Deka, Naba,Plantier-Royon, Richard,Portella, Charles
, p. 1174 - 1180 (2007/10/03)
(Chemical Equation Presented) A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two different enantiopure products: an α-aryl-α-methoxy- α-trifluoromethyl ethanal and an α-aryl-α-methoxycarboxylic acid. The overall process is eventually an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one.
Nucleophilic addition reactions of 1,4-diketones derived from tartaric acid: Synthesis of TADDOL analogues
Prasad, Kavirayani R.,Chandrakumar, Appayee
, p. 2159 - 2166 (2008/02/03)
A systematic investigation of the reduction and Grignard reagents addition to 1,4-diketones derived from tartaric acid was carried out. It was found that the reduction proceeded with high selectivity using K-Selectride as the reducing agent; while Grignar
Asymmetric synthesis of α-methoxyarylacetic acid derivatives
Prasad, Kavirayani R.,Chandrakumar, Appayee
, p. 1897 - 1900 (2007/10/03)
Stereoselective synthesis of a series of 2-aryl-2-methoxyethanols was achieved from inexpensive chiral pool tartaric acid employing a diastereoselective reduction of a symmetrical 1,4-diaryldiketone as the key step. 2-Aryl-2-methoxyethanols were enantioselectively prepared in 80-90% yield