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Highly efficient kinetic resolution of racemic secondary alkyl diazoacetates in intramolecular carbon-hydrogen insertion reactions has been achieved using chiral dirhodium(ii) carboxamidates. Products formed from catalytic diazo decomposition of racemic 2-octyl diazoacetate and, separately, its (2R)- and (2S)-enantiomeric forms, as well as bothcis- andtrans-2-methylcyclohexyl diazoacetates, have been systematically evaluated. Enantioselectivities up to 99 %ee have been obtained for -lactone formation. -Lactone production has been observed and, although minor with cyclohexyl diazoacetates, is the major insertion pathway for diazo decomposition of 2-octyl diazoacetate.Dedicated to Academician of the RAS N. S. Zefirov (on his 60th birthday).Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1798–1803, September, 1995.Financial support for this research from the National Institutes of Health (GM 46503) and the National Science Foundation of the United States is gratefully acknowledged. We thank D. A. Pierson for her preparation of 2-methylcyclohexyl diazoacetates and preliminary studies of their diazo decomposition and A. Melekhov from the Higher College of Chemistry for his preparation and catalytic studies of rac-2-octyl diazoacetate. 相似文献
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Cyril Fuhrer 《Tetrahedron letters》2004,45(22):4297-4300
The synthesis of 3a,7a-dihydro-3H,4H-furo[3,4-c]pyran-1-ones via an intramolecular hetero-Diels-Alder reaction of easily accessible α,β-unsaturated γ-ketoesters was investigated. The reaction was found to proceed in a highly stereoselective way leading to single, cis-configured product isomers. The same diastereomer is formed, independently of the configuration of the enone double bond of the precursor. The respective E- and Z-isomers react either through an endo-E-syn or an exo-Z-syn transition state. 相似文献
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Shimpei Sugiyama 《Tetrahedron letters》2006,47(49):8771-8775
The treatment of γ-lactones having a sulfinyl group at the γ-position, which were synthesized from 1-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at −78 °C gave γ-chloromagnesio γ-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated γ-chloromagnesio γ-lactones were found to be stable at below −50 °C for at least 2 h. The reaction of these γ-chloromagnesio γ-lactones with electrophiles and the stereochemistry of the reactions were investigated. 相似文献
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Tomoyuki Tajima Yukie Yamaguchi Yo-hei Shiomoto Yutaka Takaguchi 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1):2-11
Abstract We succeeded in the synthesis of a novel poly(amidoamine) dendrimer having diphenyl diselenide at the core. Modification of the dendrimer diselenide by the reaction with glucono-δ-lactone in methanol gave a water-soluble dendrimer diselenide having chiral terminal groups. The structures of dendrimers were satisfactorily confirmed by MAIDI-TOF MS spectrometry, elemental analysis, and NMR spectroscopy. Interestingly, induced circular dichroism (ICD) of the interaction between the diphenyl diselenide core and D-gluconamide periphery of the dendrimer was observed at 300 nm. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. GRAPHICAL ABSTRACT 相似文献
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Chiral γ-lactones of both enantiomers were synthesized with more than 90% optical purities. The key step was Novozym 435–catalyzed hydrolysis of racemic N-benzyl-4-acetoxyalkylamides. Additionally, because (R)-γ-lactones are predominant in apricot, mango, peach, passion fruit, and strawberry, synthesis was attempted using only one enantiomer selectively. The (R)-enantimer was synthesized with more than 80% total yield and more than 90% optical purity by a combination of Novozym 435–catalyzed hydrolysis and the Mitsunobu reaction. 相似文献
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E. V. Tikhonova S. M. Adekenov N. A. Samenov M. K. Gil'manov 《Chemistry of Natural Compounds》2001,37(1):69-71
The possible production of a new medicinal form of the antitumor preparation arglabine was studied by including it in lipoglycoprotein micelles isolated from wheat grains 相似文献
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Two new acyclic diterpene-(-lactones named hanliuine III (1) and hanliuine IV (2) were isolated from leaves of Salix matsudana (Chinese name "hanliu"). Their structures were deduced from spectral data. 相似文献
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The total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone is reported based on stereoselective reduction of δ-hydroxy β-keto ester to install 1,3-polyol system, cis Wittig olefination, and lactonization as the key steps. The synthesis of (−)-(6S,2′S)-epi cryptocaryalactone is also reported using syn-benzylidene acetal formation and a preferential Z-Wittig olefination reaction and lactonization as the key steps. 相似文献
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Masashi Hojo Tadaharu Ueda Akihiko Inoue Sumio Tokita 《Journal of Molecular Liquids》2009,148(2-3):109-113
For the purpose of improving the visible method of γ-rays detection, detailed conditions with various acids have been examined for the color development of a fluoran-based black color former in acetonitrile. It is suggested that the protons (H+), which may be produced from acid generators by γ-ray radiation, can be properly detected by the color development of the black color former containing proper kinds and concentrations of bases. Reversible decolorization through the interaction between Mg2+ and polyamines (acyclic and macrocyclic) has been examined in order to reconfirm that the colored zwitterion is produced by the direct chemical interaction with Mg (ClO4)2 in the fluoran dye–acetonitrile solution. 相似文献