Asymmetric Iodolactonization Utilizing Chiral Squaramides was written by Tungen, Joern E.;Nolsoee, Jens M. J.;Hansen, Trond V.. And the article was included in Organic Letters in 2012.Synthetic Route of C12H13FO3 The following contents are mentioned in the article:
Asym. iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst I was found to facilitate the cyclization of 5-arylhex-5-enoic acids to the corresponding iodolactones with up to 96% ee. By this protocol, unsaturated carboxylic acids are converted enantioselectively to synthetically useful δ-lactones in high yields using com. available NIS. Apparently, both hydrogen bonding and aryl/aryl interactions are important for efficient stereodifferentiation. This study involved multiple reactions and reactants, such as Methyl 5-(4-fluorophenyl)-5-oxopentanoate (cas: 149437-67-2Synthetic Route of C12H13FO3).
Methyl 5-(4-fluorophenyl)-5-oxopentanoate (cas: 149437-67-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Synthetic Route of C12H13FO3
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics