- Novel cyclization of unsaturated alcohols by phenyl selenocyanate in the presence of copper BIS(Trifluoromethanesulfonate)
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Intramolecular oxyselenenylation of unsaturated alcohols by phenyl selenocyanate with copper bis(trifluoromethanesulfonate) proceeds stereoselectively to give cyclic ethers.
- Inoue, Hirofumi,Murata, Shizuaki
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p. 847 - 850
(2007/10/03)
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- Stereoselective Cyclization of 4-Substituted 5-Hexen-1-ols and Related Compounds by Benzeneselenenyl Triflate
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Oxyselenylation of 4-substituted 5-hexen-1-ols 1 with benzeneselenenyl trifluoromethanesulfonate proceeds by intramolecular exo cyclization stereoselectively to give 3-substituted trans- or cis-2-(phenylselenenylmethyl)tetrahydropyrans 3.Formation of the trans isomers is favored when the substituents contain alkyl or phenyl substituents in the 4-position, whereas the cis isomers predominate when the substituents are alkoxyalkyl, alkoxyl, acyl, and hydroxyl.The mechanism of the trans and cis stereoselectivity is explained by steric and electronic effects in the phenylseleniranium intermediates, 7 and 8. - Key Words: Oxyselenenylation / Benzeneselenenyl triflate / Selenium compounds / Trifluoromethanesulfonate / Alkenols
- Inoue, Hirohumi,Murata, Shizuaki,Suzuki, Toshiyasu
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p. 901 - 910
(2007/10/02)
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- Stereoselectivity of Electrophile-Promoted Cyclizations of γ-Hydroxyalkenes. An Investigation of Carbohydrate-Derived and Model Substrates
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We have investigated cyclization reactions of γ-hydroxyalkenes bearing an alkoxy or alkyl substituent on the allylic carbon.A variety of electrophiles N-bromosuccinimide, N-iodosuccinimide, iodine, mercury(II) acetate, mercury(II) trifluoroacetate, mercu
- Reitz, Allen B.,Nortey, Samuel O.,Maryanoff, Bruce E.,Liotta, Dennis,Robert, Monahan
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p. 4191 - 4202
(2007/10/02)
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- CYCLIZATION OF OLEFINIC ALCOHOL BY BENZENESELENENYL TRIFLATE
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Cyclization of 4-, 5-, and 6-hydroxyalkenes with benzeneselenenyl triflate afforded corresponding tetrahydrofurans and -pyrans.
- Murata, Shizuaki,Suzuki, Toshiyasu
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p. 4297 - 4298
(2007/10/02)
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