52939-60-3Relevant articles and documents
Allylation of esters promoted by metallic dysprosium in the presence of mercuric chloride
Jia, Yu,Zhang, Mingfu,Tao, Fenggang,Zhou, Jingyao
, p. 2829 - 2835 (2002)
In the presence of mercuric chloride, the reactions of esters with allyl bromide and metallic dysprosium in anhydrous THF give diallyl alkyl carbinols in good yields. When γ-butyrolactone is used as the substrate, the corresponding product is 4-allyl-6-heptene-1, 4-diol.
Diastereotopic group selection in hydroxy-directed intramolecular C-H alkenylation of indole under oxidative palladium(II) catalysis
Kandukuri, Sandeep R.,Jiao, Lin-Yu,MacHotta, Axel B.,Oestreich, Martin
supporting information, p. 1597 - 1609 (2014/06/09)
Group-selective palladium(II)-catalyzed ring closures involving C-H bond alkenylation are reported. The cyclization precursors contain a prochiral bis(homoallylic) alcohol unit tethered to either an arene or an indole. The homobenzylic hydroxy group in these substrates is positioned to act as a directing group in the ortho-selective C-H bond activation prior to the cyclization event. Arene-derived precursors reacted poorly, even when applying a protocol that had proven effective in intermolecular hydroxy-directed C-H bond alkenylations. No asymmetric induction was obtained with chiral ligands, mono-N-protected amino acids (MPAAs) in particular. Conversely, the cyclization of indole-derived precursors was substantially more efficient, and installation of a substituent in the benzylic position rendered these intramolecular C-H bond alkenylations diastereoselective. The diastereotopic group selection is high with diastereomeric ratios ranging from dr=91:9 to 94:6.
Gem-diallylation of acyl azides with allylsamarium bromide under mild conditions
Li, Jian,Liu, Yongjun,Zhang, Yongmin
, p. 438 - 439 (2007/10/03)
Allylsamarium bromide reacts with acyl azides to give the corresponding gem-diallylation products, 4-alkyl-1,6-heptadienes-4-ols (3), in good to excellent yields. This novel reaction proceeds readily within a few minutes at room temperature.
