182816-19-9Relevant academic research and scientific papers
A simple primary amine catalyst for enantioselective α-hydroxylations and α-fluorinations of branched aldehydes
Witten, Michael R.,Jacobsen, Eric N.
, p. 2772 - 2775 (2015/06/16)
A new primary amine catalyst for the asymmetric α-hydroxylation and α-fluorination of α-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for α-functionalizations. Promising initial results in α-amination and α-chlorination reactions support this hypothesis.
Convenient routes to 2-aryl-2-fluoropropionic acids: Synthesis of monofluorinated analogues of (±)-ibuprofen, (±)-naproxen and related compounds
Goj, Olav,Kotila, Sirpa,Haufe, Guenter
, p. 12761 - 12774 (2007/10/03)
The synthesis of α-fluorinated arylpropionic acids 5 as analogues of the nonsteroidal anti-inflammatory agents (NSAIDs) flurbiprofen 1, ibuprofen 3 and naproxen 4 is accomplished by the oxidation of the corresponding primary alcohols 9. The latter are accessible on two different pathways showing their general applicability by variation of the aromatic moiety. Furthermore the influence of the fluorine substituent towards the conformation of the acid moiety in the crystal lattice is shown by comparative X-ray studies of compound 5c.
