63553-65-1Relevant academic research and scientific papers
Studies towards 1,3-diol units starting from syn β-hydroxy acylsilanes
Pavankumar Reddy, Gangireddy,Srirama Murthy, Akondi,Satyanarayana Reddy,Das, Saibal,Roisnel, Thierry,Yadav, Jhillu S.,Chandrasekhar, Srivari,Grée, René
, p. 365 - 368 (2014)
Three complementary strategies have been explored to obtain stereodefined 1,3 diols starting from easily accessible syn β-hydroxy acylsilanes: fluoride induced migrations of substituents on silicon, a Grignard addition followed by protodesilylation and Tischenko-type reactions. Preliminary data on scope and limitations of these processes are presented.
Construction of homoallylic alcohols from terminal alkynes and aldehydes with installation of syn-stereochemistry
Miura, Tomoya,Nishida, Yui,Murakami, Masahiro
, p. 6223 - 6226 (2014/05/20)
A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.
Stereo- and Regioselectivity of Reactions of Siliranes with Aldehydes and Related Substrates
Bodnar, Paul M.,Palmer, Wylie S.,Ridgway, Brian H.,Shaw, Jared T.,Smitrovich, Jacqueline H.,Woerpel
, p. 4737 - 4745 (2007/10/03)
Siliranes undergo stereoselective and regioselective insertions of benzaldehyde to provide oxasilacyclopentane products. The thermal reaction (>100°C) leads to more decomposition and side products, whereas the catalyzed variant (t-BuOK, 95%). Treatment of siliranes with enolizable aldehydes leads to silyl enol ethers. The reaction of a silirane at high temperatures with an imine leads to reductive dimerization, presumably by way of intermediate-free silylene. The mechanism for the catalyzed insertion of benzaldehyde is discussed.
Stereoselective synthesis of 1,3-diol from β-hydroxyacylsilane via rearrangement of phenyl group from silicon to carbon
Morihata, Kohdai,Horiuchi, Yoshihiro,Taniguchi, Masahiko,Oshima, Koichiro,Utimoto, Kiitiro
, p. 5555 - 5558 (2007/10/03)
Treatment of β-hydroxyacyldimethylphenylsilanes with potassium fluoride in DMSO gave 1,3-diols stereoselectively via migration of phenyl group on silicon.
Prins Reactions of Arylaldehydes, V: On the Reaction with 2-Butene and with Cyclohexene
Griengl, Herfried,Mayer, Arnulf,Geppert, Klaus Peter
, p. 1007 - 1016 (2007/10/02)
By reaction of 2--2-phenyl-1,3-dithiane (1a) with cis-2-butene oxide, subsequent reduction and acetalization c-4,t-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3a) and t-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3b) were synthesized as model compounds.For the same purpose by aldol reaction of cyclohexanone and reduction (1RS,2SR)-2cyclohexanol (7a), (1RS,2RS)-2cyclohexanol (8a), and (1RS,2RS)-2cyclohexanol (8b), and by acetalization (2α,4α,4aβ,8aβ)-2,4-bis(4-methoxyphenyl)hexahydro-4H-1,3-benzodioxin (9a) and (2α,4α,4aα,8aβ)-2,4-bis(4-nitrophenyl)hexahydro-4H-1,3-benzodioxin (10b) were obtained.From Prins reactions, starting with 2-butene 3a, c-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3c), r-4,t-5-dimethyl-c-6-phenyl-1,3,2-dioxathiane-2,2-dioxide (4), and (2Z,4E)-1,5-diphenyl-4-methyl-2,4-pentadien-1-on (5), and starting with cyclohexene (E)-3-(4-methoxybenzylidene)cyclohexenyl-4-methoxyphenyl ketone (11) have been isolated in low yields. - Keywords: Addition reactions; 1,3-Diols; 1,3-Dioxanes
