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Regioselective Ring Opening (regioselective + ring_opening)
Selected AbstractsChemInform Abstract: Studies Toward the Taming of the "Carbocation" in the Regioselective Ring Opening of Epoxides to Allylic Alcohols.CHEMINFORM, Issue 28 2010Helen A. Chapman Abstract 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. [source] Highly Regioselective Ring Opening of Epoxides and Aziridines Using (Bromodimethyl)sulfonium Bromide.CHEMINFORM, Issue 40 2006Biswanath Das Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF. [source] Regioselective Ring Opening of Amino Epoxides with Nitriles: An Easy Synthesis of (2R,3S)- and (2S,3S)-1,3-Diaminoalkan-2-ols with Differently Protected Amine Functions.CHEMINFORM, Issue 2 2006Jose M. Concellon No abstract is available for this article. [source] Synthesis of ,-Amino Alcohols by Regioselective Ring Opening of Arylepoxides with Anilines Catalyzed by Cobaltous Chloride.CHEMINFORM, Issue 6 2005Govindarajan Sundararajan Abstract For Abstract see ChemInform Abstract in Full Text. [source] Highly Regioselective Ring Opening of Epoxides Using NaN3: A Short and Efficient Synthesis of (-)-Cytoxazone.CHEMINFORM, Issue 3 2005Joshodeep Boruwa Abstract For Abstract see ChemInform Abstract in Full Text. [source] ZnI2/NaCNBH3 as an Efficient Reagent for Regioselective Ring Opening of the Benzylic Epoxide Moiety.CHEMINFORM, Issue 31 2004L. M. Funkielsztein No abstract is available for this article. [source] Highly Regioselective Ring Opening of Oxiranes with Phenoxides in the Presence of ,-Cyclodextrin in Water.CHEMINFORM, Issue 40 2003K. Surendra No abstract is available for this article. [source] Scandium Perchlorate as a Superior Lewis Acid for Regioselective Ring Opening of Aziridine Carboxylate with Indoles.CHEMINFORM, Issue 52 2002Toshio Nishikawa Abstract For Abstract see ChemInform Abstract in Full Text. [source] ChemInform Abstract: Cerium(III) Chloride Promoted Highly Regioselective Ring Opening of Epoxides and Aziridines Using NaN3 in Acetonitrile: A Facile Synthesis of 1,2-Azidoalcohols and 1,2-Azidoamines.CHEMINFORM, Issue 25 2002Gowravaram Sabitha Abstract 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. [source] ChemInform Abstract: Synthesis of Galactofuranosides by Regioselective Ring Opening of a 1,4-Anhydrogalactopyranose Derivative: A Possible Chemical Model for an Unprecedented Enzymatic Reaction.CHEMINFORM, Issue 6 2001Jose Kovensky Abstract 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. [source] Asymmetric Synthesis of ES-285, an Anticancer Agent Isolated from Marine SourcesEUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Issue 35 2009Ana C. Allepuz Abstract The asymmetric synthesis of (2S,3R)-2-amino-3-octanedecanol hydrochloride (ES-285·HCl) was achieved in eight steps in ca. 38,% overall yield from the N -benzylimine-derived from (R)-2,3- O -isopropylidene glyceraldehyde, which is easily available on gram scale from the inexpensive precursor D -mannitol. Highly diastereoselective addition of methylmagnesium bromide to the N -benzylimine was the key step to create the vic -amino alcohol moiety with the appropriate configuration. Regioselective ring opening of an intermediate aminoepoxide enabled the introduction of the long hydrocarbon chain at C4.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) [source] Benzo[a]heptalenes from Heptaleno[1,2- c]furans.HELVETICA CHIMICA ACTA, Issue 4 2007Abstract It is shown in this ,Part 2' that heptaleno[1,2- c]furans 1 react thermally in a Diels,Alder -type [4+2] cycloaddition at the furan ring with vinylene carbonate (VC), phenylsulfonylallene (PSA), , -(acetyloxy)acrylonitrile (AAN), and (1Z)-1,2-bis(phenylsulfonyl)ethene (ZSE) to yield the corresponding 1,4-epoxybenzo[d]heptalenes (cf. Schemes,1, 5, 6, and 8). The thermal reaction of 1a and 1b with VC at 130° and 150°, respectively, leads mainly to the 2,3- endo -cyclocarbonates 2,3- endo - 2a and - 2b and in minor amounts to the 2,3- exo -cyclocarbonates 2,3- exo - 2a and - 2b. In some cases, the (P*)- and (M*)-configured epimers were isolated and characterized (Scheme,1). Base-catalyzed cleavage of 2,3- endo - 2 gave the corresponding 2,3-diols 3, which were further transformed via reductive cleavage of their dimesylates 4 into the benzo[a]heptalenes 5a and 5b, respectively (Scheme,2). In another reaction sequence, the 2,3-diols 3 were converted into their cyclic carbonothioates 6, which on treatment with (EtO)3P gave the deoxygenated 1,4-dihydro-1,4-epoxybenzo[d]heptalenes 7. These were rearranged by acid catalysis into the benzo[a]heptalen-4-ols 8a and 8b, respectively (Scheme,2). Cyclocarbonate 2,3- endo - 2b reacted with lithium diisopropylamide (LDA) at ,70° under regioselective ring opening to the 3-hydroxy-substituted benzo[d]heptalen-2-yl carbamate 2,3- endo - 9b (Scheme,3). The latter was O -methylated to 2,3- endo -(P*)- 10b. The further way, to get finally the benzo[a]heptalene 13b with MeO groups in 1,2,3-position, could not be realized due to the fact that we found no way to cleave the carbamate group of 2,3- endo -(P*)- 10b without touching its 1,4-epoxy bridge (Scheme,3). The reaction of 1a with PSA in toluene at 120° was successful, in a way that we found regioisomeric as well as epimeric cycloadducts (Scheme,5). Unfortunately, the attempts to rearrange the products under strong-base catalysis as it had been shown successfully with other furan,PSA adducts were unsuccessful (Scheme,4). The thermal cycloaddition reaction of 1a and 1b with AAN yielded again regioisomeric and epimeric adducts, which could easily be transformed into the corresponding 2- and 3-oxo products (Scheme,6). Only the latter ones could be rearranged with Ac2O/H2SO4 into the corresponding benzo[a]heptalene-3,4-diol diacetates 20a and 20b, respectively, or with trimethylsilyl trifluoromethanesulfonate (TfOSiMe3/Et3N), followed by treatment with NH4Cl/H2O, into the corresponding benzo[a]heptalen-3,4-diols 21a and 21b (Scheme,7). The thermal cycloaddition reaction of 1 with ZSE in toluene gave the cycloadducts 2,3- exo - 22a and - 22b as well as 2- exo,3- endo - 22c in high yields (Scheme,8). All three adducts eliminated, by treatment with base, benzenesulfinic acid and yielded the corresponding 3-(phenylsulfonyl)-1,4-epoxybenzo[d]heptalenes 25. The latter turned out to be excellent Michael acceptors for H2O2 in basic media (Scheme,9). The Michael adducts lost H2O on treatment with Ac2O in pyridine and gave the 3-(phenylsulfonyl)benzo[d]heptalen-2-ones 28a and 3- exo - 28b, respectively. Rearrangement of these compounds in the presence of Ac2O/AcONa lead to the formation of the corresponding 3-(phenylsulfonyl)benzo[a]heptalene-1,2-diol diacetates 30a and 30b, which on treatment with MeONa/MeI gave the corresponding MeO-substituted compounds 31a and 31b. The reductive elimination of the PhSO2 group led finally to the 1,2-dimethoxybenzo[a]heptalenes 32a and 32b. Deprotonation experiments of 32a with t -BuLi/N,N,N,,N,-tetramethylethane-1,2-diamine (tmeda) and quenching with D2O showed that the most acid CH bond is HC(3) (Scheme,9). Some of the new structures were established by X-ray crystal-diffraction analyses (cf. Figs.,1, 3, 4, and 5). Moreover, nine of the new benzo[a]heptalenes were resolved on an anal. Chiralcel OD-H column, and their CD spectra were measured (cf. Figs.,8 and 9). As a result, the 1,2-dimethoxybenzo[a]heptalenes 32a and 32b showed unexpectedly new Cotton -effect bands just below 300,nm, which were assigned to chiral exciton coupling between the heptalene and benzo part of the structurally highly twisted compounds. The PhSO2 -substituted benzo[a]heptalenes 30b and 31b showed, in addition, a further pair of Cotton -effect bands in the range of 275,245,nm, due to chiral exciton coupling of the benzo[a]heptalene chromophore and the phenylsulfonyl chromophore (cf. Fig.,10). [source] | ||||||||||