- Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts: via [3,3]-sigmatropic rearrangement
-
Herein, we present a transition-metal free direct O-arylation of arylhydroxylamines employing diaryliodonium salts as arylation reagents to form transient N,O-diarylhydroxylamines that could subsequently undergo [3,3]-sigmatropic rearrangement and re-aromatization to afford structurally diverse NOBIN analogs in good to excellent yields under mild conditions.
- Du, Yuanbo,Feng, Lei,Gao, Hongyin,Guo, Lirong,Liu, Fengting,Sun, Qianyu,Yuan, Hairui
-
-
Read Online
- Catalytic asymmetric synthesis of axially chiral 2-amino-1,1′-biaryl compounds by phase-transfer-catalyzed kinetic resolution and desymmetrization
-
An efficient methodology for kinetic resolution of axially chiral 2-amino-1,1′-biaryl compounds as useful chiral building blocks was developed by means of binaphthyl-modified chiral quaternary ammonium salt-catalyzed N-allylations under phase-transfer con
- Shirakawa, Seiji,Wu, Xiangfei,Liu, Shiyao,Maruoka, Keiji
-
-
Read Online
- Synthesis and resolution of racemic 2-amino-2′-hydroxy-1,1′-binaphthyl
-
The title compound 3 has been prepared via a highly selective, Cu(II)-mediated cross-coupling of 2-aminonaphthalene 1 and 2-naphthol 2 and resolved into enantiomers via crystallization of diastereoisomeric salts with (1S)-(+)-10-camphorsulfonic acid. The method has been optimized and the use of chromatography eliminated.
- Smrcina, Martin,Vyskocil, Stepan,Polivkova, Jana,Polakova, Jana,Kocovsky, Pavel
-
-
Read Online
- Gram scale conversion of R-BINAM to R-NOBIN
-
A mild, operationally simple, and single-step transition-metal-free protocol for the synthesis of enantiomerically pure (R)-(+)-2′-amino-1,1′-binaphthalen-2-ol (R-NOBIN) from (R)-(+)-1,1′-binaphthyl-2,2′-diamine (R-BINAM) is reported. The one-pot conversion proceeds with good yield and shows no racemization. The hydroxyl on the R-NOBIN product was shown to have come from water in the reaction medium via an H218O study. The correct value of the specific rotation of R-NOBIN was reported.
- Patel, Darshan C.,Breitbach, Zachary S.,Woods, Ross M.,Lim, Yeeun,Wang, Andy,Foss, Frank W.,Armstrong, Daniel W.
-
-
Read Online
- Stereoselective Synthesis of Optically Pure 2-Amino-2′-hydroxy-1,1′-binaphthyls
-
Direct entry to optically pure 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) derivatives by an iron-catalyzed stereoselective oxidative cross-coupling reaction between 2-naphthol and 2-aminonaphthalene with a labile chiral auxiliary is reported. This efficient method offers entry to tailor-designed (Ra)- and (Sa)-NOBINs that are not accessible by any other means.
- Forkosh, Hagit,Vershinin, Vlada,Reiss, Hagai,Pappo, Doron
-
-
Read Online
- Kinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylation
-
Going through a phase: The highly selective kinetic resolution of the title compounds, which are important chiral building blocks, was achieved by phase-transfer-catalyzed N-allylation. This synthetic method was applied to the highly enantioselective desymmetrization of a biaryl compound. Copyright
- Shirakawa, Seiji,Wu, Xiangfei,Maruoka, Keiji
-
-
Read Online
- Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination
-
Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec
- Chang, Xihao,Zhang, Qinglin,Guo, Chang
-
-
Read Online
- Kinetic resolution of 1,1-biaryl-2,2-diols and amino alcohols through NHC-catalyzed atroposelective acylation
-
We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1-biaryl-2,2-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
- Lu, Shenci,Poh, Si Bei,Zhao, Yu
-
-
Read Online
- Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
-
Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
- Yu, Jeong Jae,Ryoo, Jae Jeong
-
p. 587 - 596
(2022/01/20)
-
- A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)
-
A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.
- Dyadyuk, Alina,More, Nagnath Yadav,Pappo, Doron,Shalev, Hen,Shalit, Hadas,Vershinin, Vlada
-
supporting information
p. 3676 - 3684
(2022/03/02)
-
- Mechanistic Insights into the FeCl3-Catalyzed Oxidative Cross-Coupling of Phenols with 2-Aminonaphthalenes
-
The selective FeCl3-catalyzed oxidative cross-coupling reaction between phenols and primary, secondary, and tertiary 2-aminonaphthalene derivatives was investigated. The generality of this scalable method provides a sustainable alternative for preparing N,O-biaryl compounds that are widely used as ligands and catalysts. Based on a comprehensive kinetic investigation, a catalytic cycle involving a ternary complex that binds to both the coupling partners and the oxidant during the key oxidative coupling step is postulated. Furthermore, the studies showed that the reaction is regulated by off-cycle acid-base and ligand exchange processes.
- Vershinin, Vlada,Forkosh, Hagit,Ben-Lulu, Mor,Libman, Anna,Pappo, Doron
-
-
- Enantiodivergent Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols by Dipeptide-Phosphonium Salt Catalysis Inspired by the Atherton–Todd Reaction
-
A highly enantiodivergent organocatalytic method is disclosed for the synthesis of atropisomeric biaryls via kinetic resolution inspired by a dipeptide-phosphonium salt-catalyzed Atherton–Todd (A-T) reaction. This flexible approach led to both R- and S-enantiomers by fine-tuning of bifunctional phosphonium with excellent selectivity factors (s) of up to 1057 and 525, respectively. The potential of newly synthesized O-phosphorylated biaryl diols was illustrated by the synthesis of axially chiral organophosphorus compounds. Mechanistic investigations suggest that the bifunctional phosphonium halide catalyst differentiates between the in-situ-generated P-species in the A-T process, mainly involving phosphoryl chloride and phosphoric anhydride, thus leading to highly enantiodivergent O-phosphorylation reactions. Furthermore hydrogen bonding interactions between the catalysts and phosphorus molecules were crucial in asymmetric induction.
- Chen, Yuan,Fang, Siqiang,Pan, Jianke,Ren, Xiaoyu,Tan, Jian-Ping,Wang, Tianli,Zhang, Hongkui
-
p. 14921 - 14930
(2021/05/10)
-
- Method for resolving chiral compound
-
The invention relates to the field of organic chemistry, and in particular, relates to a method for resolving a chiral compound. The method for resolving the chiral compound provided by the inventioncomprises the step of carrying out addition reaction on
- -
-
Paragraph 0077-0081
(2020/07/27)
-
- A Versatile Method for Kinetic Resolution of Protecting-Group-Free BINAMs and NOBINs through Chiral Phosphoric Acid Catalyzed Triazane Formation
-
A versatile kinetic resolution of protecting-group-free BINAMs and NOBINs has been realized through chiral phosphoric acid catalyzed triazane formation with azodicarboxylates. A series of mono-N-protected and unprotected BINAMs, diphenyl diamines and NOBIN derivatives could be kinetically resolved with excellent performances (with s factor up to 420). The gram-scale reactions and facile derivatizations of the chiral products demonstrate the potential of these methods in the asymmetric synthesis of chiral catalysts and ligands.
- Jiang, Qianwen,Liu, Wei,Yang, Xiaoyu
-
supporting information
p. 23598 - 23602
(2020/10/23)
-
- Direct Construction of NOBINs via Domino Arylation and Sigmatropic Rearrangement Reactions
-
Privileged 2-amino-2’-hydroxy-1,1’-binaphthyl (NOBIN) frameworks were constructed through a novel domino arylation of naphthylhydroxylamines with diarylhalonium salts and sigmatropic rearrangement in a transition metal-free fashion. This protocol bears broad substrate generality and proceeds under mild reaction conditions, affording diversified NOBINs in high efficiency with absolute regiocontrol during the rearrangement process. Optically active product was accessible by chiral N-heterocyclic carbene-catalyzed kinetic resolution in one pot or diastereoselective [3,3]-rearrangement guided by a removable chiral auxiliary. Remarkably, diarylchloronium and diarylbrominium salts have been employed as arylation reagents for the first time in assembling such representative biaryl frameworks.
- Zhang, Ji-Wei,Qi, Liang-Wen,Li, Shaoyu,Xiang, Shao-Hua,Tan, Bin
-
p. 1503 - 1514
(2020/09/09)
-
- DFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene
-
Guided by computational design, Tan and colleagues disclose a chiral phosphoric-acid-catalyzed asymmetric functionalization of naphthalenes with nitroso as the activating and directing group. This nucleophilic aromatic substitution reaction allows divergent access to two types of axially chiral arylindole frameworks with wide substrate generality under excellent enantiocontrol and, more importantly, offers a facile approach to the privileged NOBIN (2-amino-2′-hydroxy-1,1′-binaphthyl) structures. DFT calculations illustrate the plausible reaction pathway and provide additional insights into the origins of enantioselectivity.Functionalization of arenes represents the most efficient approach for constructing a core backbone of important aryl compounds. Compared with the well-developed electrophilic aromatic substitution and transition-metal-catalyzed C–H activation, nucleophilic aromatic substitution remains challenging because of the lack of a convenient route for rapid conversion of the σH adduct to other stable and versatile intermediates in situ. Guided by computational design, we were able to realize asymmetric nucleophilic aromatic substitution by introducing a nitroso group on naphthalene via chiral phosphoric acid catalysis. This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. Density functional theory (DFT) calculations provide further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.Highly efficient conversion of inexpensive and readily available arene materials into high-value-added chiral molecules is of great importance in modern synthetic chemistry given the enormous potential of such structures in functional materials, pharmaceuticals, and other relevant chemical industries. Organocatalytic nucleophilic aromatic substitution enabled by an azo group offers an effective approach to enantioselective functionalization of naphthalene C–H bonds featuring an intramolecular oxidation of an unstabilized σH adduct. Premised on density functional theory (DFT) calculations, nitroso has emerged as another promising activating and oxidative group, whose synthetic potential is substantiated in the atroposelective synthesis of several groups of representative biaryl atropisomers processed by a chiral phosphoric acid catalyst. The success of this reaction explicitly exemplifies the ability of computational tools to streamline organic synthesis with intensified robustness in the disclosed strategy.
- Ding, Wei-Yi,Yu, Peiyuan,An, Qian-Jin,Bay, Katherine L.,Xiang, Shao-Hua,Li, Shaoyu,Chen, Ying,Houk,Tan, Bin
-
supporting information
p. 2046 - 2059
(2020/07/13)
-
- Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols
-
An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.
- Qu, Shen,Greenhalgh, Mark D.,Smith, Andrew D.
-
supporting information
p. 2816 - 2823
(2019/02/05)
-
- CARBAZOLE DERIVATIVE AND BIPHENYL DERIVATIVE PRODUCTION METHOD AND NOVEL BIPHENYL DERIVATIVE
-
PROBLEM TO BE SOLVED: To provide a method for high-yield mass production of a carbazole derivative by a simple process using inexpensive materials. SOLUTION: A method for producing a carbazole derivative represented by general formula (3) comprises reacting an aminating agent with a 2,2'-dihydroxybiphenyl derivative represented by general formula (1). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
- -
-
Paragraph 0048-0053; 0061
(2019/05/21)
-
- Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones
-
We have developed a catalytic system based on bianthrylbis(thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3:2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.
- Otevrel, Jan,Svestka, David,Bobal, Pavel
-
supporting information
p. 5244 - 5248
(2019/06/07)
-
- Chiral aromatic amine compounds and preparation method thereof
-
The invention discloses chiral aromatic amine compounds and a preparation method thereof. The chiral aromatic amine compounds are characterized in that under the alkaline condition, compounds I reactwith compounds II to obtain corresponding products, namely chiral aromatic amine compounds labeled by compounds with structural formulas III, IV and V or enantiomers, despinners, diastereoisomers or isotopes thereof: (the formula is shown in the description), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and R17 are separately selected from any group, and X is chlorine or bromine. The chiral aromatic amine compounds with high optical purity (an ee value is greater than 99 percent) have wide application in the fields of bioactivity, materials, chiral ligands, chiral catalysts and the like, and can be further derived to prepare recemic or chiral aromatic amine ligands serving as catalyst for asymmetric catalytic reaction. The invention lays a foundation for developing novel catalysts for the asymmetric catalytic reaction and has economic practicality and industrial application prospect.
- -
-
Paragraph 0022-0025
(2018/05/16)
-
- One-pot heterocyclic ring closure of 1,1′-bi-2-naphthol to 7H-dibenzo[c,g]carbazole
-
An operationally simple ring closure of racemic 1,1′-bi-2-naphthol (BINOL) yielded the heterocyclic aromatic compound 7H-dibenzo[c,g]carbazole (DBC). This one-pot method gave a good conversion and is suitable for gram-scale synthesis. DBC derivatives have high thermal durability, amorphous and crystalline structures with unique morphological properties, and semi-conducting behavior with potential applications in organic electronics.
- Hassan, Fathy,Kawamoto, Masuki,Salikolimi, Krishnachary,Hashizume, Daisuke,Hirose, Takuji,Ito, Yoshihiro
-
supporting information
p. 99 - 102
(2017/12/28)
-
- Fluxionally chiral DMAP catalysts: Kinetic resolution of axially chiral biaryl compounds
-
Can organocatalysts that incorporate fluxional groups provide enhanced selectivity in asymmetric transformations? To address this issue, we have designed chiral 4-dimethylaminopyridine (DMAP) catalysts with fluxional chirality. These catalysts were found
- Ma, Gaoyuan,Deng, Jun,Sibi, Mukund P.
-
supporting information
p. 11818 - 11821
(2015/03/13)
-
- A general and facile approach for the synthesis of 2'-functionalized 1,1'-binapthyl-2-ols
-
A facile and efficient protocol for the synthesis of 2'-functionalized 1,1'-binaphthyl-2-ols has been developed. The C,O-dilithio reagent (2) generated by the reductive ring-opening of binaphthofuran (1) with lithium was treated with the corresponding electrophiles to give 2'-functionalized 1,1'-binaphthyl-2-ols including the halides (3), amine (4), acid (5), aldehyde (6), carbonate (7) or phosphonate (8), respectively, in moderate to good yields.
- Xie, Xiaomin,Ding, Lina,Ni, Gang,Zhang, Zhaoguo,Gao, Jinsheng
-
experimental part
p. 1630 - 1634
(2011/07/08)
-
- Highly efficient chromatographic resolution of α,α′- dihydroxybiaryls
-
(Graph Presented) Separation factors as high as 115 were observed for the chromatographic resolution of many α,α′-dihydroxybiaryls with a single chiral stationary phase made from readily available amino acid derivatives. The stationary phase works well for biphenyl-type compounds. It works extremely well for larger bis-aromatic compounds, such as binaphthyl-type compounds.
- Huang, Junmin,Li, Tingyu
-
p. 5821 - 5823
(2007/10/03)
-
- Synthesis of a tridentate ligand for use in TiIV-catalyzed acetate aldol addition reactions
-
A facile, practical synthesis and resolution of (±) -2′-amino-[1,1′-binaphthalen]-2-ol (1) is described, as well as the preparation of the tridentate Schiff base ligand 2 derived from condensation of 1 with 3-bromo-5-(tert-butyl)salicylaldehyde, which has been used in catalytic enantioselective acetate aldol addition reactions.
- Singer, Robert A.,Brock, Jane R.,Carreira, Erick M.
-
p. 1040 - 1044
(2007/10/03)
-
- Ligands based on chiral 2-amino-2′-hydroxy-1,1′-binaphthyl and related frameworks for asymmetric catalysis
-
The present invention includes array of new chiral ligands that are optically active or racemic. These ligands are bidentate, tridentate, tetradentate or pentadentate ligands which include P-P, P-N, N-N, mixed P-N, Schiff base or carbene sites. The present invention further includes a catalyst prepared by a process, which includes contacting a transition metal salt, or a complex thereof, and a ligand according to the present invention. The present invention still further includes a process for preparation of an asymmetric compound. In this process, a substrate capable of forming an asymmetric product by an asymmetric reaction and a catalyst according to the present invention are contacted to produce an asymmetric product. Transition metal complexes with these ligands are effective catalysts for asymmetric reactions. Applicant has discovered that asymmetric products can be prepared using the chiral catalysts according to the present invention in enantioselective reactions, such as hydrogenation, hydroformylation, Michael addition, Heck reaction, Aldol reaction, allylic alkylation, cyclopropanation, epoxidation, and olefin metathesis.
- -
-
-
- A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN)
-
A practical synthesis of 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) was realized from BINOL through a single step. Its facile purification procedure makes the process amenable for large scale synthesis of NOBIN.
- K?rber, Karsten,Tang, Wenjun,Hu, Xinquan,Zhang, Xumu
-
p. 7163 - 7165
(2007/10/03)
-
- Preparation of 2-amino-2'-hydroxy-1,1'-binaphthyl and N-arylated 2- amino-1,1'-binaphthyl derivatives via palladium-catalyzed amination
-
Palladium-catalyzed amination reactions were carried out with 2- triflato-2'-(4-methoxybenzyloxy)-1,1'-binaphthyl (5) and benzophenone imine followed by hydrolysis of the imine and hydrogenolysis of the benzyl protecting group to afford 2-amino-2'-hydroxy-1,1'-binaphthyl (1). Arylamines were also coupled successfully with 5 under similar conditions.
- Singer, Robert A.,Buchwald, Stephen L.
-
p. 1095 - 1098
(2007/10/03)
-
- Chiral enrichment of 2-amino-2'-hydroxy-1,1'-binaphthyl
-
A new synthetic procedure for the formation of 2-amino-2'-hydroxy-1,1'- binaphthyl, and a new purification procedure through the formation of Schiff bases, purification of the Schiff bases, and breakdown of the Schiff bases through amine exchange, are described. Through the new purification procedure, greater than 99% purity of the compound can be obtained easily and reliably. A set of procedures were examined to compare the efficiency and reliability to resolve 2-amino-2'-hydroxy-1,1'-binaphthyl into enantiomers. A new procedure was discovered to enrich enantiomeric excess from less than 10% to 95-99% in one step. Even a racemic mixture from an achiral procedure can be enriched to 67% e.e. in about 4% yield. The X-ray crystal structure of the racemic mixture [rhombohedral, space group Iba2, a=15.718(2) A, b=21.703(2) A, c=8.5398(9) A, V=2913.2(5) A3, RI=0.0705, Z=8, d(calcd)=1.301 g/cm3, F(000)=1200 e] was solved to elucidate the intriguing behavior of this compound.
- Mahmoud, Hussein,Han, Ying,Segal, Brent M.,Cai, Lisheng
-
p. 2035 - 2042
(2007/10/03)
-
- Novel two-phase oxidative cross-coupling of the two-component molecular crystal of 2-naphthol and 2-naphthylamine
-
Two-phase reaction of a two-component molecular crystal of 2-naphthol and 2-naphthylamine suspended in aqueous Fe3+ solutions gives a cross-coupling product, 2-amino-2′-hydroxy-1,1′-binaphthalene, with good selectivity.
- Ding, Kuiling,Xu, Qiguo,Wang, Yang,Liu, Jinxia,Yu, Zhengyan,Du, Baoshi,Wu, Yangjie,Koshima, Hideko,Matsuura, Teruo
-
p. 693 - 694
(2007/10/03)
-
- Selective Cross-Coupling of 2-Naphthol and 2-Naphthylamine Derivatives. A Facile Synthesis of 2,2',3-Trisubstituted and 2,2',3,3'-Tetrasubstituted 1,1'-Binaphthyls
-
The novel 1,1'-binaphthyls with OH and/or NHR (R = H or Ph) groups in the 2,2'-positions and with additional methoxycarbonyl group(s) in the 3- or 3,3'-positions (13-18) have been synthesized from their respective precursors 1-5 by the CuCl2/t-BuNH2-mediated oxidative cross-coupling.In most cases, the chemoselectivity was good, and the cross-coupled products 11-18 were obtained in fair to excellent yields.Binaphthyls 6-10, resulting from the selfcoupling, and carbazoles 19-23 have been identified as byproducts.Ab initio calculations and electrochemical measurements have been employed to account for the observrd selectivity.
- Smrcina, Martin,Vyskocil, Stepan,Maca, Bohumil,Polasek, Miroslav,Claxton, Thomas A.,et al.
-
p. 2156 - 2163
(2007/10/02)
-