113567-15-0Relevant articles and documents
Enantioselective dihydroxylation of olefins by osmium tetroxide in the presence of an optically active 1,1'-binaphthyl diamine derivative
Rosini, Carlo,Tanturli, Roberto,Pertici, Paolo,Salvadori, Piero
, p. 2971 - 2982 (1996)
The chiral diamine (S)-1, introduced by Cram and Mazaleyrat, has been reprepared following a different sequence which involves the resolution of diacid (RS)-3. The e.e. (via HPLC and NMR), the absolute configuration (via CD) and the most stable conformation (via UV and molecular mechanics calculations) of (S)-1 have been determined. (S)-1 has been employed as a chiral auxiliary in the stoichiometric syn-dihydroxylation of olefins obtaining optically active 1,2-diols with e.e.s up to 98%.
Reductive Ullmann coupling of aryl halides by palladium nanoparticles supported on cellulose, a recoverable heterogeneous catalyst
Rasouli, Mohammad Ali,Ranjbar, Parviz Rashidi
, p. 946 - 950 (2013)
Palladium nanoparticles supported on cellulose were prepared without using any reducing agent and used as a highly efficient catalyst for the Ullmann reductive coupling of aryl halides in the presence of zinc, in a water-alcohol mixture as solvent in air. The obtained palladium nanoparticles were characterized by scanning electron microscopy (SEM), FTIR, thermogravimetric analysis (TGA) and ICP-AES analysis. The synthesis of biaryls from chloroarenes was performed by this catalyst with good yield. The catalyst remains stable up to 75 °C and can be recovered and reused several times without loss of activity.
A practical synthesis of C2-symmetric chiral binaphthyl ketone catalyst
Seki,Yamada,Kuroda,Imashiro,Shimizu
, p. 1677 - 1680 (2000)
A practical synthesis of 11-membered C2-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (±)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(±)-6] was efficiently resolved by (R)-(-)-1-cyclohexylethylamine to give (R)-6 in >99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 °C provided the desired chiral ketone (R)-1 in 61-63% yield without need for high dilution techniques.
Enantioselective catalysis of the triplex diels-alder reaction: A study of scope and mechanism
Kim, Ji-In,Schuster, Gary B.
, p. 9309 - 9317 (1992)
Irradiation of the chiral sensitizers 1,1-bis(2,4-dicyanonaphthalene) and 1,r-bis(2,10-dicyanoanthracene) catalyzes the triplex Diels-Alder reaction of trans-β-methylstyrene with 1,3-cyclohexadiene to form the [4 + 2] cycloadducts endo-trans-6-methyl-5-phenylbicyclo[2.2.2]oct-2-ene. When the sensitizer is optically active and the irradiation is performed at low temperature in ether or toluene solution, the [4 + 2] cycloadducts are formed enantioselectively. The mechanism of the enantioselective triplex Diels-Alder reaction was examined by chemical and spectroscopic means. Interaction of the chiral sensitizer with the prochiral styrene forms diastereomeric exciplexes. The equilibration of these exciplexes is fast at room temperature but not at low temperature. The exciplexes react with diene to form a triplex. This reaction leads to cycloadduct formation. Enantioselection is a consequence of different trapping efficiencies for the diastereomeric exciplexes by diene.
Red or near-infrared light operating negative photochromism of a binaphthyl-bridged imidazole dimer
Kometani, Aya,Inagaki, Yuki,Mutoh, Katsuya,Abe, Jiro
, p. 7995 - 8005 (2020)
The development of red or near-infrared light (NIR) switchable photochromic molecules is required for an efficient utilization of sunlight and regulation of biological activities. While the photosensitization of photochromic molecules to red or NIR light has been achieved by a two-photon absorption process, the development of a molecule itself having sensitivity to red or NIR light has been now a challenging study. Herein, we developed an efficient molecular design for realizing red or NIR-light-responsive negative photochromism based on binaphthyl-bridged imidazole dimers. The introduction of electron-donating substituents shows the red shift of the absorption band at the visible-light region because of the contribution of a charge-transfer transition. Especially, the introduction of a di(4-methoxyphenyl)amino group (TPAOMe) and a perylenyl group largely shifts the absorption edge of the stable colored form to 900 nm. In addition, because the absorption band of one of the derivatives substituted with TPAOMe covers the whole visible-light region, the colored form shows a neutral gray color. Upon red (660 nm) or NIR-light (790 nm) irradiation, we observed the negative photochromic reaction from the stable colored form to the metastable colorless form. Therefore, the substituted binaphthyl-bridged imidazole dimers constitute the attractive photoswitches within a biological window.
Synthesis method of axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid
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, (2016/10/10)
The invention relates to the technical field of bromination, hydrolysis, oxidation and coupling reaction in organic synthesis, particularly a synthesis method of an axially chiral dinaphthalene ligand precursor (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method comprises the following steps: synthesizing a compound 1-bromo-2-methylnaphthalene from an initial raw material 2-bromomethylnaphthalene, carrying out bromination, hydrolysis and oxidation on the 1-bromo-2-methylnaphthalene to obtain 1-bromo-2-naphthoic acid, generating an ester under the actions of methanol and thionyl chloride, protecting the carboxyl group, carrying out Ullmann reaction under the action of copper powder to perform coupling, carrying out hydrolysis to obtain 2,2'-dinaphthyl-1,1'-dicarboxylic acid, and finally, resolving to obtain the (s)-2,2'-dinaphthyl-1,1'-dicarboxylic acid. The method is simple to operate, and has the advantages of higher yield and favorable economical efficiency.
Design and synthesis of new stable fluorenyl-based radicals
Tian, Yi,Uchida, Kazuyuki,Kurata, Hiroyuki,Hirao, Yasukazu,Nishiuchi, Tomohiko,Kubo, Takashi
, p. 12784 - 12793 (2015/02/19)
Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.
Synthesis of axially chiral amino acid derivatives via the selective monoesterification of 1,1′-biaryl-2,2′-dicarboxylic acids
Furuta, Takumi,Nikaido, Masanori,Yamamoto, Junya,Kuribayashi, Toshifumi,Kawabata, Takeo
, p. 1312 - 1318 (2013/07/05)
Axially chiral amino acid derivatives were synthesized via a selective single-step monoesterification of 1,1′-binaphthyl-2,2′-dicarboxylic acids. In the presence of Ag2CO3, the alkylative monoesterification of a 1,1′-binaphthyl-2,2′-dicarboxylic acid with an alkyl halide proceeded selectively in a single operation. Curtius rearrangement of the monomethyl ester and successive alcoholysis of the corresponding isocyanate afforded the N-protected binaphthyl amino acids. Georg Thieme Verlag Stuttgart, New York.
Synthesis of (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin oxide and preliminary studies on its use in the oxidation of sulfides
Procter, David J.,Rayner, Christopher M.
, p. 2975 - 2987 (2007/10/03)
The first synthesis (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]- selenepin oxide 1 has been achieved from (R)-(+)-1,1'-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1'-bi-2-naphthol. Palladium catalyzed alkoxy-carbonylation of ditriflate 4 gave dimethyl ester 5 which was then reduced and the resultant diol converted to key intermediate chloride 8. Cyclization with sodium selenolate gave novel enantiomerically pure selenide 9, which upon oxidation yielded the desired selenoxide (R)-1. Preliminary studies on the oxidation of sulfides to sulfoxides using 1 and 2,2,2-trifluoroethane sulfonic acid are also described.
A Convenient Synthesis of Optically Pure Dimethyl 1,1'-Binaphthalene-2,2'-dicarboxylate from 1,1'-Binaphthalene-2,2'-diol
Ohta, Tetsuo,Ito, Masata,Inagaki, Kohji,Takaya, Hidemasa
, p. 1615 - 1616 (2007/10/02)
Optically pure dimethyl 1,1'-binaphthalene-2,2'-dicarboxylate has been prepared by methoxycarbonylation of ditriflate of 1,1'-binaphthalene-2,2'-diol catalyzed by Pd(OAc)2-dppp-N,N-diisopropylethylamine in the presence of methanol under CO atmosphere in 83percent yield.
