87514-09-8Relevant articles and documents
Nucleophilic epoxidation of α′-hydroxy vinyl sulfoxides
Fernandez de la Pradilla, Roberto,Fernandez, Jorge,Manzano, Pilar,Mendez, Paloma,Priego, Julian,Tortosa, Mariola,Viso, Alma,Martinez-Ripoll, Martin,Rodriguez, Ana
, p. 8166 - 8177 (2007/10/03)
The nucleophilic epoxidation of a variety of α′-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et2O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,Ss) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,Ss) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.
Stereochemically defined cyclohexanediols through the regioselective ring-opening of silylated epoxy alcohols
Adam, Waldemar,Prein, Michael,Richter, Markus J.
, p. 1231 - 1234 (2007/10/03)
The nucleophilic ring-opening of the silylated epoxy alcohol 2 leads to highly functionalized building blocks of defined stereochemistry, whereby the regioselectivity may be controlled through the proper choice of the nucleophilic and the reaction conditi
Reactions of 2-phenylthio-2-cycloalkenones and 2-[phenyl(thiomethyl)]-2-cycloalkenones. Synthesis of some useful chiral and achiral intermediates
Vankar,Kumaravel,Bhattacharya,Vankar,Kaur
, p. 4829 - 4840 (2007/10/02)
The allyl acetates derived from 2-phenylthio-2-cyclopentenone, 2-phenylthio-2-cyclohexenone, 2-[phenylthio(methyl)]-2-cyclopentenone and 2-[phenylthio(methyl)]-2-cyclohexenone have been hydrolysed by pig liver acetone powder to obtain the corresponding al
Enantiocomplementary resolution of 2-phenylthio-2-cyclopentenol and 2-phenylthio-2-cyclohexenol using the same lipase
Takano,Yamada,Iida,Ogasawara
, p. 592 - 596 (2007/10/02)
Both racemic 2-phenylthio-2-cyclopentenol (±)-(3a) and 2-phenylthio-2-cyclohexenol (±)-(3b) afford the corresponding (R)-acetates (R)-4a,b and the unreacted (S)-alcohols (S)-3a,b, respectively, in excellent optical and chemical yields on treatment with vi
CLEAVAGE OF SILICON-VINYL CARBON BOND BY nBu4NF
Oda, Hiroji,Sato, Mitsuyoshi,Morizawa, Yoshitomi,Oshima, Koichiro,Nozaki, Hitosi
, p. 2877 - 2880 (2007/10/02)
Dimethylphenylsilyl- and diphenylmethylsilyl-vinyl carbon bonds are cleaved with nBu4NF.Desilylation of 1-phenylthio-1-trimethylsilyl-1-alkenes in the presence of aldehyde moiety gives carbanion adducts.