- Chiral phosphine nitrogen phosphine ligand and chiral metal organic coordination complex and application
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The invention discloses a chiral phosphine nitrogen phosphine ligand and chiral metal organic coordination complex and application. The chiral tridentate phosphine nitrogen phosphine ligand is shown as a formula (I), and the chiral metal organic coordination complex is shown as a formula (II), wherein the chiral metal organic coordination complex shown as the formula (II) is used as a homogeneouscatalyst to be applied to preparation of phenylalanine derivatives with high optical activity. The novel chiral nitrogen-phosphine ligand synthesized by taking cheap amino acid as a chiral source is applied to asymmetric hydrogenation reaction, and a chiral product with relatively high yield can be obtained with relatively low catalytic dosage, relatively short reaction time and relatively mild reaction conditions.
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Paragraph 0069-0071
(2020/07/02)
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- Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
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Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
- Marcum, Justin S.,Roberts, Courtney C.,Manan, Rajith S.,Cervarich, Tia N.,Meek, Simon J.
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supporting information
p. 15580 - 15583
(2017/11/14)
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- Insights into the mechanism for gold catalysis: Behaviour of gold(i) amide complexes in solution
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We report the synthesis and activity of new mononuclear and dinuclear gold amide complexes 1-7. The dinuclear complexes 6b and 7 were characterised by single crystal X-ray analysis. We also report solution NMR and freezing point depression experiments to rationalise their behaviour in solution and question the de-ligation process invoked in gold catalysis.
- Bobin, Mariusz,Day, Iain J.,Roe, Stephen M.,Viseux, Eddy M. E.
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p. 6592 - 6602
(2013/07/26)
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- Gold amides as anticancer drugs: Synthesis and activity studies
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Modular gold amide chemotherapeutics: Access to modern chemotherapeutics with robust and flexible synthetic routes that are amenable to extensive customisation is a key requirement in drug synthesis and discovery. A class of chiral gold amide complexes featuring amino acid derived ligands is reported herein. They all exhibit in vitro cytotoxicity against two slow growing breast cancer cell lines with limited toxicity towards normal epithelial cells. The Royal Society of Chemistry 2013.
- Newcombe, Sonya,Bobin, Mariusz,Shrikhande, Amruta,Gallop, Chris,Pace, Yannick,Yong, Helen,Gates, Rebecca,Chaudhuri, Shuvashri,Roe, Mark,Hoffmann, Eva,Viseux, Eddy M. E.
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supporting information
p. 3255 - 3260
(2013/06/05)
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- Chiral aminophosphines as catalysts for enantioselective double-michael indoline syntheses
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The bisphosphine-catalyzed double-Michael addition of dinucleophiles to electron-deficient acetylenes is an efficient process for the synthesis of many nitrogencontaining heterocycles. Because the resulting heterocycles contain at least one stereogenic center, this double-Michael reaction would be even more useful if an asymmetric variant of the reaction were to be developed. Aminophosphines can also facilitate the double-Michael reaction and chiral amines are more readily available in Nature and synthetically; therefore, in this study we prepared several new chiral aminophosphines. When employed in the asymmetric double-Michael reaction between ortho-tosylamidophenyl malonate and 3-butyn-2-one, the chiral aminophosphines produced indolines in excellent yields with moderate asymmetric induction.
- Khong, San N.,Kwon, Ohyun
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p. 5626 - 5650
(2012/07/03)
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- Chiral proline-based P,O and P,N ligands for iridium-catalyzed asymmetric hydrogenation
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Two new classes of proline-based P,O and P,N ligands were prepared and applied in the iridium-catalyzed asymmetric hydrogenation of alkenes. Both types of ligands induced high enantioselectivities in the hydrogenation of trisubstituted C=C bonds. Iridium complexes derived from P,O ligands bearing sterically demanding amide or urea groups at the pyrrolidine N-atom proved to be especially efficient catalysts for the conjugate reduction of α,β-unsaturated esters and ketones, whereas analogous P,N ligands led to better results with dialkyl-phenyl-substituted alkenes and an allylic alcohol as substrates.
- Rageot, Denise,Pfaltz, Andreas
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p. 2176 - 2193
(2013/02/23)
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- Proline-based P,O ligand/iridium complexes as highly selective catalysts: Asymmetric hydrogenation of trisubstituted alkenes
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P,O joins the mix: P,O ligands (L1) form efficient iridium catalysts for the asymmetric hydrogenation of olefins. The proline-derived ligands lead to high enantioselectivities with several classes of alkenes, most notably with α,β-unsaturated carboxylic e
- Rageot, Denise,Woodmansee, David H.,Pugin, Benoet,Pfaltz, Andreas
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p. 9598 - 9601
(2011/12/05)
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- Rational design of organocatalyst: Highly stereoselective michael addition of cyclic ketones to nitroolefins
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A remarkable organocatalyst that facilitates the asymmetric Michael addition of cyclic ketones to nitroolefins in excellent stereoselectivities (98:2 to > 99:1 dr, 92% to > 99% ee) has been developed and afforded various types of optically active nitroalk
- Tan, Bin,Zeng, Xiaofei,Lu, Yunpeng,Chua, Pei Juan,Zhong, Guofu
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supporting information; experimental part
p. 1927 - 1930
(2009/09/25)
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- METHOD FOR THE PREPARATION OF AMINOPHOSPHINE LIGANDS AND THEIR USE IN METAL CATALYSTS
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The present application is directed to i) a two-step method for synthesizing phosphme-ammophosphme (P,N,P) ligands, ii) the use of such ligands in the preparation of metal complexes as hydrogenation catalysts, and iii) ammophosphme (P,N) and phosphme-ammo
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Page/Page column 41
(2009/01/24)
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- Synthesis of building blocks for the development of the SUPRAPhos ligand library and examples of their application in catalysis
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We have previously introduced the SUPRAPhos ligand library, which is based on components that are self-assembled through nitrogen-zinc interactions, and report here an extension of this library, which widens the scope for application in asymmetric homogeneous catalysis. For example, we report the synthesis of phosphorus amidite appended porphyrins and building blocks with stereogenic centers at the phosphorus. With the new building blocks described in this paper we can form a 450-membered SUPRAPhos library, which is based on 45 building blocks (30 pyridyl phosphorus ligands and 15 complementary porphyrin-appended phosphorus ligands). Examples of the use of members of the library in the rhodium-catalyzed asymmetric hydroformylation of styrene are included. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Goudriaan, P. Elsbeth,Jang, Xiao-Bin,Kuil, Mark,Lemmens, Renske,Van Leeuwen, Piet W. N. M.,Reek, Joost N. H.
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scheme or table
p. 6079 - 6092
(2009/05/31)
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- N-Boc-L-valine-connected amidomonophosphane rhodium(I) catalyst for asymmetric arylation of N-tosylarylimines with arylboroxines
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A catalytic asymmetric arylation of sterically tuned imines with arylboroxines was developed by using N-Boc-L-valine-connected amidomonophosphane rhodium(I) catalyst in n-PrOH. The TMS group used for the steric tuning of imines is convertible to other fun
- Kuriyama, Masami,Soeta, Takahiro,Hao, Xinyu,Chen, Qian,Tomioka, Kiyoshi
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p. 8128 - 8129
(2007/10/03)
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- A long-range chiral relay via tertiary amide group in asymmetric catalysis: new amino acid-derived N,P-ligands for copper-catalysed conjugate addition.
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New N,P-ligands 4-6, derived from valinol and prolinol, respectively, have been developed for the asymmetric, copper(I)-catalysed conjugate addition of diethylzinc to unsaturated ketones; the tertiary amide group has been shown to effectively relay the chiral information from the ligand backbone to the active centre.
- Malkov, Andrei V,Hand, John B,Kocovsky, Pavel
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p. 1948 - 1949
(2007/10/03)
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- An efficient procedure for the preparation of (E)-α-alkylidenecycloalkanones mediated by a CeCl3·7H2O-NaI system. Novel methodology for the synthesis of (S)-(-)-pulegone
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2-Alkylidenecycloalkanones are powerful synthons used as the key intermediates in many important syntheses. Because of their potential, a general method of preparation from readily available starting materials, under very mild conditions, was considered to be worthwhile. Cerium(III) chloride heptahydrate in combination with sodium iodide in refluxing acetonitrile promotes a regio- and stereoselective β-elimination reaction to (E)-2-alkylidenecycloalkanones in 2-(1-hydroxyalkyl)cycloalkanones. The synthetic value of the present procedure is demonstrated by the synthesis of monoterpene (S)-(-)-pulegone (8) in its optically active form.
- Bartoli, Giuseppe,Bosco, Marcella,Dalpozzo, Renato,Giuliani, Arianna,Marcantoni, Enrico,Mecozzi, Tiziana,Sambri, Letizia,Torregiani, Elisabetta
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p. 9111 - 9114
(2007/10/03)
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- Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds
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A catalytic asymmetric conjugate addition reaction of organocopper reagents, generated from copper salt, a chiral phosphine, and Grignard reagent, with cyclohexenone is highly dependent on the counter anion of copper species, solvents, Grignard reagents,
- Kanai, Motomu,Nakagawa, Yuichi,Tomioka, Kiyoshi
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p. 3843 - 3854
(2007/10/03)
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- Structural requirements of an external, chiral amidophosphine ligand for asymmetric reaction of an organocopper reagent
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Three types of an external, chiral amide ligand, 2-6, were prepared and examination of their behavior in an asymmetric conjugate addition reaction of lithium dimethylcuprate with chalcone revealed to possibility for steric tuning to realize high selectivity.
- Nakagawa, Yuichi,Kanai, Motomu,Nagaoka, Yasuo,Tomioka, Kiyoshi
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p. 7805 - 7808
(2007/10/03)
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