In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwis... more In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwise unreactive copper acetylides add to enones present as s-trans conformers to provide good yields of the silyl enol ethers of -acetylido carbonyl compounds. Typically good substrates are 2-cyclopentenone, 2-cyclohexenone, R, -unsaturated aldehydes, and -alkoxy-R-enones. Copper acetylide reagents prepared from CuI and an alkynyllithium give considerably higher yields than those prepared from CuBr or CuCN. Iodotrimethylsilane is by far the most efficient silane, although trimethylsilyl triflate is useful in some cases.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iod... more Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90 % and diastereoselectivities from 80 to 93%. The dominating diastereomers are different from those formed with LiR2Cu/TMSCl or in copper(l)-mediated addition of Grignard reagents. Corresponding additions to enoylamides of O-tritylprolinol also give high yields of conjugate adducts, but lower diastereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
H NMR spectral characteristics of synthetic trans and cis arylcoumarans and their acetates which ... more H NMR spectral characteristics of synthetic trans and cis arylcoumarans and their acetates which are related to 8-5' neolignans are given. This information is used to reassign structures to neolignans reported in nine papers, from the cis to the frans 7-aryl-8-hydroxymethyl configurations, and to neolignans in six papers in which no assignments were made. Thus far, there is no evidence for the occurrence of 8-5' neolignans with a cis configuration in nature. 0 1997
... Tetrahedron Letters 39 (1998) 24132416 Synthesis of Cinnamaldehydes, Esters of Cinnamic Acids... more ... Tetrahedron Letters 39 (1998) 24132416 Synthesis of Cinnamaldehydes, Esters of Cinnamic Acids and Acylals of Cinnamaldehydes by Oxidation of Arylpropenes with 2,3Dicyano5,6 dichlorobenzoquinone (DDQ Tommy Iliefski, Shiming ... 11. Olstein, R.; Stephenson, EFM Aust. ...
Methylal (7.6 g) and phosphorus pentoxide (2.84 g) were added to a stirred solution of eugenol (6... more Methylal (7.6 g) and phosphorus pentoxide (2.84 g) were added to a stirred solution of eugenol (6) (1.64 g) in chloroform (20 ml, dried over phosphorus pentoxide) [cf. the method for the methoxymethylation of alcohols described by ]. After 2 h the reaction mixture was poured into ice-T. Iliefski et al.: Lignin-Related Cinnamaldehydes 479 Holzforschung / Vol. 57 / 2003 / No. 5
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwis... more In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwise unreactive copper acetylides add to enones present as s-trans conformers to provide good yields of the silyl enol ethers of -acetylido carbonyl compounds. Typically good substrates are 2-cyclopentenone, 2-cyclohexenone, R, -unsaturated aldehydes, and -alkoxy-R-enones. Copper acetylide reagents prepared from CuI and an alkynyllithium give considerably higher yields than those prepared from CuBr or CuCN. Iodotrimethylsilane is by far the most efficient silane, although trimethylsilyl triflate is useful in some cases.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iod... more Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90 % and diastereoselectivities from 80 to 93%. The dominating diastereomers are different from those formed with LiR2Cu/TMSCl or in copper(l)-mediated addition of Grignard reagents. Corresponding additions to enoylamides of O-tritylprolinol also give high yields of conjugate adducts, but lower diastereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
H NMR spectral characteristics of synthetic trans and cis arylcoumarans and their acetates which ... more H NMR spectral characteristics of synthetic trans and cis arylcoumarans and their acetates which are related to 8-5' neolignans are given. This information is used to reassign structures to neolignans reported in nine papers, from the cis to the frans 7-aryl-8-hydroxymethyl configurations, and to neolignans in six papers in which no assignments were made. Thus far, there is no evidence for the occurrence of 8-5' neolignans with a cis configuration in nature. 0 1997
... Tetrahedron Letters 39 (1998) 24132416 Synthesis of Cinnamaldehydes, Esters of Cinnamic Acids... more ... Tetrahedron Letters 39 (1998) 24132416 Synthesis of Cinnamaldehydes, Esters of Cinnamic Acids and Acylals of Cinnamaldehydes by Oxidation of Arylpropenes with 2,3Dicyano5,6 dichlorobenzoquinone (DDQ Tommy Iliefski, Shiming ... 11. Olstein, R.; Stephenson, EFM Aust. ...
Methylal (7.6 g) and phosphorus pentoxide (2.84 g) were added to a stirred solution of eugenol (6... more Methylal (7.6 g) and phosphorus pentoxide (2.84 g) were added to a stirred solution of eugenol (6) (1.64 g) in chloroform (20 ml, dried over phosphorus pentoxide) [cf. the method for the methoxymethylation of alcohols described by ]. After 2 h the reaction mixture was poured into ice-T. Iliefski et al.: Lignin-Related Cinnamaldehydes 479 Holzforschung / Vol. 57 / 2003 / No. 5
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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