180348-04-3Relevant academic research and scientific papers
Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage
Shibatomi, Kazutaka,Kitahara, Kazumasa,Okimi, Takuya,Abe, Yoshiyuki,Iwasa, Seiji
, p. 1388 - 1392 (2016/02/05)
The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditio
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.
New synthetic routes to 2-fluoro-2-phenylalkanoic acids
Goj, Olav,Haufe, Guenter
, p. 1289 - 1294 (2007/10/03)
2-Fluoro-2-phenylalkanoic acids 2 are obtained by oxidation of the corresponding β-fluoro-β-phenyl alcohols 6. These compounds are shown to be accessible by two alternative pathways, either by bromo fluorination of α-alkyl styrenes 3, subsequent bromine-b
