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Synthesis of Enantiopure Trifluoromethyl Building Blocks via a Highly Chemo- and Diastereoselective Nucleophilic Trifluoromethylation of Tartaric Acid-Derived Diketones.
- Source :
-
Journal of Organic Chemistry . 2/16/2007, Vol. 72 Issue 4, p1174-1180. 7p. 6 Diagrams, 3 Charts. - Publication Year :
- 2007
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 72
- Issue :
- 4
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24095416
- Full Text :
- https://doi.org/10.1021/jo062016z