85250-56-2Relevant academic research and scientific papers
Direct synthesis of allyl sulfides from allyl alcohols and thiols
Tsay,Lin,Furth,Shum,King,Yu,Chen,Hwu
, p. 329 - 334 (2007/10/02)
In the presence of boron trifluoride-diethyl ether complex, various allyl alcohols [(-)-myrtenol, geraniol, cinnamyl alcohol, linalool, 1-octen-3-ol, 2-hydroxybenzyl alcohol and bicyclic diols] were reacted with thiophenol, 1-butanethiol, trimethyl(phenylthio)silane or hexamethylsilane in dichloromethane at room temperature to give the corresponding allyl sulfides in good to excellent yields. The mild conditions for this transformation allowed chemoselectivity.
Regiocontrol in copper-catalyzed grignard reactions with allylic substrates
B?ckvall, Jan-E.,Sellén, Mikael,Grant, Brian
, p. 6615 - 6621 (2007/10/02)
The regiochemistry of copper-catalyzed reactions between Grignard reagents and allylic substrates has been studied. A dual regiocontrol was obtained in the Li2CuCl4-catalyzed Grignard reaction with primary allylic acetates. Reaction
The Preparation of Some Octenyl Sulfides from Oct-1-en-3-ol and Oct-2-en-1-ol
Binns, Malcolm R.,Haynes, Richard K.,Lambert, Dale E.,Schober, Paul A.,Turner, Susan G.
, p. 281 - 290 (2007/10/02)
(E)- and (Z)-1-(Phenylthio)oct-2-ene, (E)-1-(methylthio)- and 1-(t-butylthio)-oct-2-ene, S- N,N-dimethylthiocarbamate, S- N,N-dimethylthiocarbamate, (E)-(oct-2-enylthio)benzothiazole, and S- N,N,N',N'-tetramethylphosphorodiamidothioate have been prepared by nucleophilic substitution reactions and - and -sigmatropic shifts involving intermediates prepared from oct-1-en-3-ol and (E)- and (Z)-oct-2-en-1-ol.
The use of metal reagents in stereo- and regioselective functionalizations of conjugated dienes
Baeckval, Jan-E
, p. 665 - 670 (2007/10/02)
Conjugated dienes have been selectively functionalized via 1-acetoxy-4-chloro-2-alkenes and via 2-(phenylsulfonyl)-1,3-dienes.In both these approaches nucleophiles can be added to the 1- and 4-positions.It was shown that also non-stabilized carbon nucleophiles (from cuprates or copper(I)-catalyzed Grignard reactions) can be used.The utility of the functionalizations was demonstrated by the syntheses of a marine natural product and a butterfly pheromone.Finally, the 2-(phenyl-sulfonyl)-1,3-dienes show a dual electron demand in Diels-Alder reactions and give cycloadducts with both electron-rich and electron-deficient olefins.
A Dual Regiocontrol in the Copper-catalysed Grignard Reaction with Primary Allylic Acetates
Baeckvall, Jan-E.,Sellen, Michael
, p. 827 - 829 (2007/10/02)
The reaction of primary allylic acetates with Grignard reagents in the presence of catalytic amounts of Li2CuCl4 can be regiochemically controlled to give either α- or γ-substitution of the allylic acetoxy group.
A ROUTE TO PROSTAGLANDIN PRECURSORS FROM 1-(PHENYLTHIO)-2-OCTENYLLITHIUM.
Binns, Malcolm R.,Haynes, Richard K.,Lambert, Dale E.,Schober, Paul A.
, p. 3385 - 3388 (2007/10/02)
The enolates generated by the conjugate addition of 1-(phenylthio)-2-octenyllithium to 4-tert-butoxycyclopent-2-en-1-one and γ-crotonolactone react with methyl 7-halohept-5-ynoates in the presence of Ph3SnCl to deliver products which may be converted into prostaglandin precursors.
Synthesis of Substituted Indans as Prostacyclin Analogues
Phialas, Memnon,Sammes, Peter G.,Kennewell, Peter D.,Westwood, Robert
, p. 687 - 695 (2007/10/02)
A route is described to the substituted indans (8) and (10), prepared as analogues of prostaglandin I2 (prostacyclin).Two key steps in the synthesis involve the regiospecific attack of lithium salts from allylic sulphides onto indene oxides and, after oxidation to the corresponding sulphoxides, their reductive rearrangement to the required diols.Using model indene oxides, attempts have been made to direct the stereochemistry of the exocyclic hydroxy group by steric control during formation of the precursor sulphide.
