14774-35-7Relevant articles and documents
STEREOSPECIFIC SYSNTHESIS OF (+/-)-β-SANTALOL
Sato, Kikumasa,Miyamoto, Osamu,Inoue, Seiichi,Honda, Kiyoshi
, p. 1183 - 1184 (1981)
A sterospecific sysnthesis of 1-acetoxy-5-bromo-2-methyl-2-cis-pentene in 4 steps starting from 3-formyl-5,6-dihydro-2H-pyran, dimer of acrolein, followed by alkylation of 2-ethoxycarbonyl-3-methylbicyclo(2.2.1)hept-2-ene with the bromide furnished a facile sysnthesis of (+/-)-β-santalol.
Chiral hetero- and carbocyclic compounds from the asymmetric hydrogenation of cyclic alkenes
Verendel, J. Johan,Li, Jia-Qi,Quan, Xu,Peters, Byron,Zhou, Taigang,Gautun, Odd R.,Govender, Thavendran,Andersson, Pher G.
supporting information; experimental part, p. 6507 - 6513 (2012/06/29)
Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes 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. Copyright