100757-24-2Relevant academic research and scientific papers
Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes
Kimura, Masanari,Ezoe, Akihiro,Mori, Masahiko,Iwata, Keisuke,Tamaru, Yoshinao
, p. 8559 - 8568 (2007/10/03)
Ni(acac)2 catalyzes homoallylation of aldehydes with 1,3-dienes in the presence of triethylborane. Triethylborane serves as a reducing agent delivering a formal hydride to the C2 position of 1,3-dienes, thus generating a formal homoallyl anion species and enabling the novel homoallylation of aldehydes. The reaction proceeds smoothly at room temperature in the absence of any phosphane or nitrogen ligands and is highly regioselective and stereoselective for a wide variety combination of aldehydes and 1,3-dienes: e.g., isoprene and benzaldehyde combine to give a mixture of anti- and syn-1-phenyl-3-methyl-4-penten-1-ol (2.2) in a ratio of 15:1 in 90% yield. Under the conditions, sterically congested aliphatic aldehydes and ketones show low yields. In such cases, diethylzinc serves as a substitute for triethylborane and yields the expected products in good yields with similarly high regio- and stereoselectivity. 1,3-Cyclohexadiene is one exception among 24 kinds of dienes examined and undergoes allylation (not homoallylation) selectively.
Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol
Feldman,Simpson
, p. 6985 - 6988 (2007/10/02)
(E)-Selective oxygenation of 1,2-disubstituted alkenylcyclopropanes, and subsequent SmI2 mediated cleavage of the 1,2-dioxolane products with retention of stereochemistry, leads to a concise synthesis of the plant metabolite (±)-yashabushitriol.
Oxygenation of Substituted Vinylcyclopropanes: Preparative and Mechanistic Studies
Feldman, Ken S.,Simpson, Robert E.
, p. 4878 - 4886 (2007/10/02)
1-Vinylcyclopropanes bearing phenyl, vinyl, or ester substituents at C(2) of the cyclopropyl ring or alkyl groups at C(1) of the vinyl moiety were subjected to phenylthio or phenylseleno radical catalyzed oxygenation to furnish the corresponding substitut
Stereoselective Intramolecular Iodoetherification of 4-pentene-1,3-diols: Synthesis of cis-2-(Iodomethyl)-3-hydroxytetrahydrofurans
Tamaru, Yoshinao,Hojo, Makoto,Kawamura, Shin-ichi,Sawada, Shuji,Yoshida, Zen-ichi
, p. 4062 - 4072 (2007/10/02)
Intramolecular iodoetherification of 4-pentene-1,3-diol and its monosubstituted derivatives, irrespective of the substitution pattern, provides cis-2-(iodomethyl)-3-hydroxytetrahydrofurans in high yields.The cis selectivity generally exceeds 95percent .So
