848873-48-3Relevant academic research and scientific papers
Stereocontrolled intramolecular meta-arene-alkene photocycloaddition reactions using chiral tethers: Efficiency of the tether derived from 2,4-pentanediol
Sugimura, Takashi,Yamasaki, Akiko,Okuyama, Tadashi
, p. 675 - 683 (2007/10/03)
Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility.
