Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes was written by Verendel, J. Johan;Li, Jia-Qi;Quan, Xu;Peters, Byron;Zhou, Taigang;Gautun, Odd R.;Govender, Thavendran;Andersson, Pher G.. And the article was included in Chemistry – A European Journal in 2012.COA of Formula: C6H8O2 This article mentions the following:
Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asym. hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes, e.g., I, with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes, e.g., II, was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates. In the experiment, the researchers used many compounds, for example, 5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7COA of Formula: C6H8O2).
5,6-Dihydro-2H-pyran-3-carbaldehyde (cas: 13417-49-7) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.COA of Formula: C6H8O2
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics