- Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones
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Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1
- Yuan, Shuai,Zeng, Qingle,Wang, Jiajun,Zhou, Lihong
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supporting information
p. 32 - 42
(2021/02/09)
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- Asymmetric Baeyer-Villiger oxidation: Classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization of: Meso -disubstituted cycloketones
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Regioselectivity is a crucial issue in Baeyer-Villiger (BV) oxidation. To date, few reports have addressed asymmetric BV oxidation of 3-substituted cycloketones due to the high difficulty of controlling regio- and stereoselectivity. Herein, we report the asymmetric BV oxidation of 3-substituted and meso-disubstituted cycloketones with chiral N,N′-dioxide/Sc(iii) catalysts performed in three ways: classical kinetic resolution, parallel kinetic resolution and desymmetrization. The methodology was applied in the total and formal synthesis of bioactive compounds and natural products. Control experiments and calculations demonstrated that flexible and adjustable catalysts played a significant role in the chiral recognition of substrates.
- Wu, Wangbin,Cao, Weidi,Hu, Linfeng,Su, Zhishan,Liu, Xiaohua,Feng, Xiaoming
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p. 7003 - 7008
(2019/07/31)
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- A novel, C2-symmetric, chiral bis-cyclosulfinamide-olefin tridentate ligand in Rh-catalyzed asymmetric 1,4-additions
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A C2-symmetric, chiral bis-cyclosulfinamide-olefin ligand composed of two 1-oxo-2,3-dihydro-1,2-benzisothiazole moieties with rigid skeletons and a conformationally flexible butenylene chain is disclosed for the first time. HRMS and 1/sup
- Zhang, Li,Tan, Mingchao,Zhou, Lihong,Zeng, Qingle
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supporting information
p. 2778 - 2783
(2018/06/11)
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- Synthesis of Highly Enantioenriched Propelladienes and their Application as Ligands in Asymmetric Rh-Catalyzed 1,4-Additions
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The first synthesis of highly enantioenriched [4.3.3]propelladienes is reported. The novel bridged bicyclo[3.3.0] dienes were applied as steering ligands in the rhodium-catalyzed asymmetric arylation of cyclic enones. The catalytic system showed high catalytic activity, and the 1,4-adducts were obtained in good to excellent yields (46-99%) with enantioselectivities up to 96% ee.
- Pecchioli, Tommaso,Christmann, Mathias
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supporting information
p. 5256 - 5259
(2018/09/13)
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- Dicyclic sulfamide-alkene chiral ligand as well as preparation method and application
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The invention discloses a dicyclic sulfamide-alkene chiral ligand as well as a preparation method and application. The structural characteristic of the dicyclic sulfamide-alkene chiral ligand is thatthe chiral ligand is a C2 symmetric compound formed by c
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Paragraph 0025-0032
(2021/05/13)
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- PHOSPHINE-OLEFIN LIGAND HAVING FACE ASYMMETRIC CYCLOPENTADIENYL-MANGANESE COMPLEX IN BASIC SKELETON
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PROBLEM TO BE SOLVED: To provide a face asymmetric ligand for a transition metal catalyst asymmetric reaction high in yield and optical purity to not only a cyclic enone compound, but also various enone compounds containing an aliphatic enone compound. SO
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Paragraph 0124; 0128
(2017/06/27)
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- Planar-chiral phosphine-olefin ligands exploiting a (Cyclopentadienyl)manganese(I) scaffold to achieve high robustness and high enantioselectivity
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A series of 2-methyl-1,3-propenylene-bridged (η5-diarylphosphinocyclopentadienyl)(phosphine)manganese(I) di-carbonyl complexes 2 have been developed as a new class of phosphine-olefin ligands based on a planar-chiral transition-metal scaffold,
- Kamikawa, Ken,Tsen, Ya-Yi,Jian, Jia-Hong,Takahashi, Tamotsu,Ogasawara, Masamichi
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supporting information
p. 1545 - 1553
(2017/02/10)
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- Chiral Bicyclic Bridgehead Phosphoramidite (Briphos) Ligands for Asymmetric Rhodium-Catalyzed 1,2- and 1,4-Addition
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A complementary solution for Rh-catalyzed enantioselective 1,2- and 1,4-arylation with two structurally related chiral ligands is reported. A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from 1-aminoindane was efficient for the 1,2-arylation of N-sulfonyl imines, while that derived from 1,2,3,4-tetrahydro-1-naphthylamine was efficient for 1,4-arylation of α,β-unsaturated cyclic ketones. For α,β-unsaturated N-tosyl ketimines, the briphos derived from 1-aminoindane was found to selectively provide γ, γ-diaryl N-tosyl enamines with high yields and stereoselectivities.
- Lee, Ansoo,Kim, Hyunwoo
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p. 3520 - 3527
(2016/05/24)
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- Chiral Phosphorus-Olefin Ligands for the RhI-Catalyzed Asymmetric Addition of Aryl Boronic Acids to Electron-Deficient Olefins
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New chiral phosphorus-olefin hybrid ligands derived from the rigid "privileged" l-proline have been conveniently prepared and applied in the rhodium-catalyzed asymmetric arylation of electron-deficient olefins with arylboronic acids at room temperature; t
- Chen, Qian,Li, Liang,Zhou, Guangli,Ma, Xiaoli,Zhang, Lu,Guo, Fang,Luo, Yi,Xia, Wujiong
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supporting information
p. 1518 - 1522
(2016/06/01)
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- A chiral phosphine-olefin ligand derived from l-hydroxyproline and its use in the rhodium-catalyzed asymmetric 1,4-addition
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A new chiral phosphine-olefin ligand (S)-1 has been designed and synthesized from l-hydroxyproline via a short reaction sequence. It was examined for its efficiency in the rhodium-catalyzed asymmetric addition of arylboronic acids and a phenylzinc reagent
- Gandi, Vasudeva Rao,Lu, Yixin,Hayashi, Tamio
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p. 679 - 682
(2015/08/03)
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- The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions
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We have designed the first chiral diene-based metal-organic framework (MOF), E2-MOF, and postsynthetically metalated E2-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond fo
- Sawano, Takahiro,Ji, Pengfei,McIsaac, Alexandra R.,Lin, Zekai,Abney, Carter W.,Lin, Wenbin
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p. 7163 - 7168
(2015/11/23)
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- Flexible C2-symmetric bis-sulfoxides as ligands in enantioselective 1,4-addition of boronic acids to electron-deficient alkenes
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The application of acyclic C2-symmetric chelating bis-sulfoxide ligands in the Rh(I)-catalyzed enantioselective 1,4-addition of boronic acids to electron-deficient alkenes is reported. Among the acyclic ethane-bridged bis-sulfoxides tested, the
- Khiar, Noureddine,Salvador, Alvaro,Valdivia, Victoria,Chelouan, Ahmed,Alcudia, Ana,Alvarez, Eleuterio,Fernandez, Inmaculada
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p. 6510 - 6521
(2013/07/26)
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- Application of chiral N-tert-butylsulfinyl vinyl aziridines in Rh(i) catalyzed 1,4-addition of aryl boronic acids to cyclic enones
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Chiral N-tert-butylsulfinyl vinyl aziridine ligands prepared from a readily available (R)-tert-butanesulfinamide have been applied in the rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones, which gives high yields and excelle
- Chen, Qian,Chen, Chao,Guo, Fang,Xia, Wujiong
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supporting information
p. 6433 - 6435
(2013/08/23)
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- Convenient in situ generation of a chiral bis-N-heterocyclic carbene palladium catalyst and its application in enantioselective synthesis
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To simplify catalytic reactions employing chelating bisNHC-metal complexes, studies were conducted to elucidate conditions for the in situ generation of a chiral chelating bisNHC-palladium catalyst from the corresponding diimidazolium salt. The method provides a convenient entry to catalytic reactions and eliminates catalyst preparation steps. In addition to the in situ prepared catalyst, for comparative purposes, isolable species were synthesized and characterized by NMR spectroscopy, combustion analysis, and single-crystal X-ray diffraction. Employing C2-symmetric ligands derived from trans-9,10-Dihydro-9,10-EthanoAnthracene-11,12-diyl (DEA) and trans-9,10-Dihydro-9,10-EthanoAnthracene-11,12-diylMethanediyl (DEAM), diNHC-Pd complexes were synthesized and tested for activity in enantioselective arylboronic acid addition to cyclic enones.
- Mullick, Amrita B.,Jeletic, Matthew S.,Powers, Andrew R.,Ghiviriga, Ion,Abboud, Khalil A.,Veige, Adam S.
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p. 810 - 819
(2013/07/05)
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- Chiral dihydrobenzofuran-based diphosphine (BICMAP): Optical resolution and application to rhodium(I)-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to cyclic enones
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Chiral dihydrobenzofuran-based diphosphine ligand (BICMAP) 1 was used as a ligand for the rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to cyclic enones up to 99% ee. We also found that the BICMAP-rhodium system was an efficient catalyst for the 1,4-addition of alkenylboronic acids to 2-cyclohexenone in good enantioselectivities.
- Mino, Takashi,Hashimoto, Masatoshi,Uehara, Katsunori,Naruse, Yoshiaki,Kobayashi, Shohei,Sakamoto, Masami,Fujita, Tsutomu
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supporting information; experimental part
p. 4562 - 4564
(2012/09/25)
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- Polymer-incarcerated chiral Rh/Ag nanoparticles for asymmetric 1,4-addition reactions of arylboronic acids to enones: Remarkable effects of bimetallic structure on activity and metal leaching
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Robust and highly active bimetallic Rh nanoparticle (NP) catalysts, PI/CB Rh/Ag, have been developed and applied to the asymmetric 1,4-addition of arylboronic acids to enones without leaching of the metals. We found that the structures of the bimetallic Rh/Ag catalysts and chiral ligands strongly affect their catalytic activity and the amount of metal leaching. PI/CB Rh/Ag could be recycled several times by simple operations while keeping high yields and excellent enantioselectivities. To show the versatility of the PI/CB Rh/Ag catalyst, a one-pot, oxidation-asymmetric 1,4-addition reaction of an allyl alcohol and an arylboronic acid was demonstrated by combining the PI/CB Rh/Ag catalyst with PI/CB Au as an aerobic oxidation catalyst.
- Yasukawa, Tomohiro,Miyamura, Hiroyuki,Kobayashi, Shu
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p. 16963 - 16966
(2013/01/15)
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- Cu-catalyzed enantioselective 1,4-additions of aryl-Grignard reagents to cyclohexenone in the presence of TADDOL-derived phosphane-phosphite ligands
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Asymmetric conjugate additions (1,4-additions) of aryl-Grignard reagents to cyclohex-2-enone, currently a more or less unsolved challenge, were investigated. For this purpose, a small library of phenol-derived chiral phosphane-phosphite ligands containing TADDOL- or BINOL-based phosphite moieties was evaluated. These ligands are easily prepared by a short modular scheme previously developed in this laboratory. Two particularly powerful ligands (4a and 4b, both TADDOL-derived and each possessing a bulky tert-butyl substituent ortho to the phosphite group) were identified. Conditions were optimized with use of the addition of (4-methoxyphenyl)magnesium bromide to cyclohexenone as a standard reaction system. Under optimized conditions [CuBr·SMe 2 (4 mol-%), ligand 4a (6 mol-%), 2-methyl-THF, -78 °C, slow addition of Grignard reagent] the 1,4-product was obtained with high enantioselectivity (up to 95 % ee) and good regioselectivity (r.r. = 90:10). The scope of the method was probed with different aryl-Grignard reagents. It was found that reagents with electron-donating substituents in meta- or para-positions performed particularly well, whereas the presence of F or CF 3 substituents led to decreased ee values. Only ortho-substituted aryl-Grignard reagents did not give rise to useful results. A series of phosphane-phosphite ligands were also tested in the Rh-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone, but enantioselectivities did not exceed 70 % ee in this case. The difficult task of employing aryl-Grignard reagents in Cu-catalyzed enantioselective 1,4 addition reactions was achieved with the assistance of readily accessible chiral modular P,P ligands. High enantioselectivities were obtained in a number of synthetically relevant cases. Copyright
- Naeemi, Qaseem,Dindaroglu, Mehmet,Kranz, Darius P.,Velder, Janna,Schmalz, Hans-Guenther
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experimental part
p. 1179 - 1185
(2012/04/10)
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- (S)-Phenylalanine-derived chiral phosphorus-olefin ligands in rhodium-catalyzed asymmetric 1,4-addition reactions
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Chiral phosphorus-olefins (S)-1, (S)-4, and (S)-5 have been designed and synthesized. These ligands were all synthesized from (S)-phenylalanine derivatives and act as phosphorus-olefin bidentate ligands to rhodium. The coordination face of the olefin can
- Narui, Rintaro,Hayashi, Sayuri,Otomo, Haruka,Shintani, Ryo,Hayashi, Tamio
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experimental part
p. 284 - 293
(2012/06/16)
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- Design of N-cinnamyl sulfinamides as new sulfur-containing olefin ligands for asymmetric catalysis: Achieving structural simplicity with a categorical linear framework
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The design and development of an extraordinarily interesting new class of chiral sulfur-olefin hybrid ligands with remarkable structural simplicity were described. These unique sulfinamide-olefin ligands have been proved to be highly effective ligands in rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids to α,β-unsaturated carbonyl compounds (up to 99% yield and 98% ee).
- Jin, Shen-Shuang,Wang, Hui,Zhu, Ting-Shun,Xu, Ming-Hua
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supporting information; experimental part
p. 1764 - 1768
(2012/04/23)
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- Synthesis and characterization of κ-2-bis-N-heterocyclic carbene rhodium(I) catalysts: Application in enantioselective arylboronic acid addition to cyclohex-2-enones
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This manuscript describes the synthesis and characterization of new derivatives of di-N-heterocyclic carbene (diNHC) ligands derived from trans-9,10-dihydro-9,10-ethanoanthracene-11,12-diylmethanediyl (DEAM) and trans-9,10-dihydro-9,10-ethanoanthracene-11
- Jeletic, Matthew S.,Lowry, Roxy J.,Swails, Jason M.,Ghiviriga, Ion,Veige, Adam S.
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supporting information; experimental part
p. 3127 - 3134
(2011/10/09)
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- Readily accessible chiral diene ligands for Rh-catalyzed enantioselective conjugate additions of boronic acids
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Enabled by the broad scope of the Pd-catalyzed asymmetric alkylation of meso- and d,l-divinylethylene carbonate, several chiral diene ligands were prepared in two steps from commercial materials. Subsequently, these ligands were evaluated in the Rh-catalyzed asymmetric conjugate addition of boronic acids to enones.
- Trost, Barry M.,Burns, Aaron C.,Tautz, Thomas
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supporting information; experimental part
p. 4566 - 4569
(2011/10/09)
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- Chiral sulfoxide-olefin ligands: Completely switchable stereoselectivity in rhodium-catalyzed asymmetric conjugate additions
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Have it both ways: A novel class of chiral sulfoxide-olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium-catalyzed 1,4-additions of arylboronic acids to electron-deficient olefins, and remarkable olefin-directed reversal of stereoselectivity (up to >99 ee, R isomer; 98 ee, S isomer) was observed when the reversal ligand pair L1 (branched olefin) and L2 (linear olefin) were utilized (see scheme). Copyright
- Chen, Guihua,Gui, Jiangyang,Li, Liangchun,Liao, Jian
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supporting information; experimental part
p. 7681 - 7685
(2011/10/17)
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- Chiral N-tert-butanesulfinyl α,β-unsaturated ketimine: A simple and highly effective olefin/sulfinimide hybrid ligand for asymmetric 1,4-additions
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One novel type of chiral olefin/sulfinimide hybrid ligands has been developed through a simple one-step condensation of α,β-unsaturated ketones with tert-butanesulfinamide and utilized successfully for rhodium-catalyzed asymmetric conjugated additions to furnish the desired adducts in high yields with excellent ee's.
- Feng, Xiangqing,Wei, Beibei,Yang, Jing,Du, Haifeng
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supporting information; experimental part
p. 5927 - 5929
(2011/10/08)
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- A class of benzene backbone-based olefin-sulfoxide ligands for Rh-catalyzed enantioselective addition of arylboronic acids to enones
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A class of readily available and easily tunable benzene backbone-based olefin-sulfoxide ligands was developed for the rhodium-catalyzed asymmetric conjugate addition reaction of arylboronic acids to enones with up to 97% yield and 97% ee.
- Xue, Feng,Li, Xincheng,Wan, Boshun
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experimental part
p. 7256 - 7262
(2011/10/09)
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- Design of N-sulfinyl homoallylic amines as novel sulfinamide-olefin hybrid ligands for asymmetric catalysis: Application in Rh-catalyzed enantioselective 1,4-additions
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Here we show that simple and readily available chiral sulfinamide-olefins can display great catalytic activities and enantioselectivities in rhodium-catalyzed 1,4-addition reactions. This study represent the first example of chiral sulfur-based olefin ligand class for transition metal-catalyzed asymmetric transformation.
- Jin, Shen-Shuang,Wang, Hui,Xu, Ming-Hua
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supporting information; experimental part
p. 7230 - 7232
(2011/08/09)
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- A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: Synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids
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The synthesis of a novel C2-symmetric bisphosphane ligand was accomplished starting from trans-(2R,3R)-bis(3′,5′-diphenylphenyl) cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,
- Goek, Yaar,Noel, Timothy,Eycken, Johan Van Der
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experimental part
p. 2768 - 2774
(2011/03/18)
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- Monodentate non-C2-symmetric chiral N-heterocyclic carbene complexes for enantioselective synthesis. Cu-catalyzed conjugate additions of aryl- and alkenylsilylfluorides to cyclic enones
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(Chemical Equation Presented) A new class of enantioselective conjugate addition (ECA) reactions that involve aryl- or alkenylsilyl fluoride reagents and are catalyzed by chiral non-C2-symmetric Cu-based N-heterocyclic carbene (NHC) complexes a
- Lee, Kang-Sang,Hoveyda, Amir H.
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body text
p. 4455 - 4462
(2009/09/30)
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- A chiral bis-sulfoxide ligand in late-transition metal catalysis; rhodium-catalyzed asymmetric addition of arylboronic acids to electron-deficient olefins
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A bis-sulfoxide with a binaphthyl backbone is introduced as a readily available, chiral ligand entity in late-transition metal catalysis. Ligand p-tol-BINASO [where p-tol-BINASO is 1,1′-binaphthalene-2,2′-diyl-bis-(p-tolylsulfoxide)] is obtained in pure f
- Mariz, Ronaldo,Luan, Xinjun,Gatti, Michele,Linden, Anthony,Dorta, Reto
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p. 2172 - 2173
(2008/09/18)
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- Asymmetric Ni-catalyzed conjugate allylation of activated enones
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The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The rea
- Sieber, Joshua D.,Morken, James P.
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p. 4978 - 4983
(2008/09/20)
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- Rhodium-catalyzed asymmetric conjugate additions of boronic acids to enones using DIPHONANE: A novel chiral bisphosphine ligand
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The synthesis of a novel enantiopure C2-symmetric bisphosphine, DIPHONANE, was accomplished starting from 2,5-norbornadione, utilizing (R,R)- and/or (S,S)-(2,3-O-di[(phenylamino)carbonyl]tartaric acid for the resolution of an intermediate phosp
- Vandyck, Koen,Matthys, Bavo,Willen, Mario,Robeyns, Koen,Van Meervelt, Luc,Van Der Eycken, Johan
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p. 363 - 366
(2007/10/03)
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- Application of rhodium complexes of chiral diphenylphosphino-functionalized N-heterocyclic carbenes as catalysts in enantioselective conjugate additions of arylboronic acids
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The Rh complex 1a of (S,S)-1-(2-diphenylphosphanylnaphthalen-1-yl)-3-(2- isopropylphenyl)-4,5-diphenylimidazolidin-2-ylidene was found to promote enantioselective conjugate additions of arylboronic acids to enones and α,β-unsaturated esters with up to 98%
- Becht, Jean-Michel,Bappert, Erhard,Helmchen, Guenter
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p. 1495 - 1498
(2007/10/03)
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- Planar-chiral cyrhetrenes for the rhodium-catalyzed asymmetric 1,4-addition and the hydrogenation of enamides
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The syntheses of novel cyrhetrenes 7a-c and 8a,b are described. These planar-chiral, mono- and diphosphines have been applied as ligands in the Rh-catalyzed 1,4-addition reaction to activated olefins and in the Rh-catalyzed hydrogenation of enamide 12, giving the corresponding products with up to 97 and 93% ee, respectively.
- Stemmler, Rene T.,Bolm, Carsten
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p. 9925 - 9931
(2007/10/03)
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- Asymmetric Addition of Aryl Boron Reagents to Enones with Rhodium Dicyclophane Imidazolium Carbene Catalysis
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Chiral N-heterocyclic carbene ligands based on [2.2]paracyclophanes form complexes with rhodium. These catalysts can be used in the high-yielding and enantioselective asymmetric conjugate addition of arylboron compounds to cyclic and acyclic enones (see scheme).
- Ma, Yudao,Song, Chun,Ma, Changqing,Sun, Zhijun,Chai, Qiang,Andrus, Merritt B.
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p. 5871 - 5874
(2007/10/03)
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- Rhodium-catalyzed asymmetric 1,4-addition of aryltitanium reagents generating chiral titanium enolates: Isolation as silyl enol ethers
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The addition of aryltitanium triisopropoxide (ArTi(OPr-i )3) to α,β-unsaturated ketones proceeded with high enantioselectivity (94-99.8% ee) in the presence of 3 mol % of [Rh(OH)((S )-binap)]2 in THF at 20 °C to give high yields of t
- Hayashi, Tamio,Tokunaga, Norihito,Yoshida, Kazuhiro,Han, Jin Wook
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p. 12102 - 12103
(2007/10/03)
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- Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones
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The asymmetric 1,4-addition reaction of arylboronic acids with cycloalkenones was catalyzed by 1 mol% of an amidomonophosphine-rhodium(I) catalyst in a 10:1 mixture of dioxane and water at 100°C, affording 3-arylcycloalkanones in reasonably high enantiose
- Kuriyama, Masami,Tomioka, Kiyoshi
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p. 921 - 923
(2007/10/03)
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- BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids
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matrix presented BINOL-based diphosphonites having achiral backbones are useful ligands in the Rh-catalyzed conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds. The nature of the achiral backbone determines the direction and degr
- Reetz, Manfred T.,Moulin, Dominique,Gosberg, Andreas
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p. 4083 - 4085
(2007/10/03)
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- Stereospecificity and Absolute Stereochemistry of Bifunctional Amidine-Catalyzed 1,3-Proton Transfer in 1,3-Disubstituted Cyclohexenes
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The stereochemistry of the reversible 1,3-proton transfer of 3-phenyl-1-(2-tolyl)cyclohexene ((A)) to 1-phenyl-3-(2-tolyl)cyclohexene ((B)), catalyzed by the bifunctional catalyst 1,2,3,4,4a,5,6,7-octahydro-1,8-naphthyridine ((C)), has been studied in ben
- Ek, Marianne,Ahlberg, Per
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p. 211 - 218
(2007/10/02)
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