18559-89-2Relevant academic research and scientific papers
Facile Preparation of Functionalized 1-Substituted Cycloalkenes via an Iodine Atom Transfer Radical Addition-Elimination Process
Meyer, Daniel,Vin, Estelle,Wyler, Benjamin,Lapointe, Guillaume,Renaud, Philippe
supporting information, p. 745 - 748 (2016/03/12)
An efficient and scalable two-step one-pot procedure for the preparation of cycloalkenes substituted with a functionalized alkyl side chain is reported. This method is based on a triethylborane-mediated iodine atom transfer radical addition (ATRA) of 1-io
Stereoseleetive Syntheses of β,γ-Unsaturated Esters and γ-Lactones: 1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected =CCH2CO2Et Synthon Equivalent
Katritzky, Alan R.,Feng, Daming,Lang, Hengyuan
, p. 4131 - 4136 (2007/10/03)
l-(Benzotriazol-l-yl)-3-(diphenylphosphoryl)-l-ethoxy-l-propene (3), prepared from N-(α-ethoxyallyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced β,γ-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding γ,γ-disubstituted β,γ-unsaturated esters 11a-d or γ-lactones 9a-c and 13. A double lithiation process provided β,γ,γ-trisubstituted β,γ-unsaturated esters 15, 18, and β,γ,γ-trisubstituted γ-lactone 14.
Direct Conversion of β,γ-Unsaturated Esters into Lactones Induced by TMS-I
Piva, Olivier
, p. 13687 - 13696 (2007/10/02)
β,γ-unsaturated esters readily prepared by photodeconjugation are converted in one step into butanolides by treatment with TMS-I.The reaction has been extended to the access to α-alkylidene lactones.
Palladium(0)-Catalyzed Alkoxycarbonylation of Allyl Phosphates and Acetates
Murahashi, Shun-Ichi,Imada, Yasushi,Taniguchi, Yuki,Higashiura, Shinya
, p. 1538 - 1545 (2007/10/02)
Palladium-catalyzed alkoxycarbonylation of allyl phosphates under CO (1 atm) at 50 deg C proceeds highly efficiently to give the corresponding β,γ-unsaturated esters.The carbonylation of geranyl phosphate ((E)-11) under CO (1 atm) at 50 deg C gave ethyl ester of homogeranic acid ((E)-12) stereoselectively.The carbonylation takes place at least substituted allylic positions with inversion of configuration.Typically, the methoxycarbonylation of cis-5-(methoxycarbonyl)-2-cyclohexen-1-yl phosphate (cis-16) gave trans-dimethyl-2-cyclohexene-1,5-dicarboxylate (trans-17) selectively.Alkoxycarbonylation of allyl acetates is performed for the first time in the presence of a catalytic amount of bromide ion.The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium(0) species to allyl acetates to give ?-allylpalladium acetate, fast ligand exchange of the acetate with bromide, insertion of carbon monoxide to give acylpalladium species, and alkoxylation.
PALLADIUM(O)-CATALYZED CARBONYLATION OF ALLYL PHOSPHATES AND ALLYL ACETATES. SELECTIVE SYNTHESIS OF β,γ-UNSATURATED ESTERS.
Murahashi, Shun-Ichi,Imada, Yasushi,Taniguchi, Yuki,Higashiura, Shin-ya
, p. 4945 - 4948 (2007/10/02)
Palladium catalyzed carbonylations of allyl phosphates and allyl acetates give β,γ-unsaturated esters efficiently.The latter reaction requires bromide ion as a co-catalyst.
