105836-14-4Relevant articles and documents
Chiral Arene Chromium Tricarbonyl Complexes as Enantioselective Catalysts: Highly Selective 1,2-Alkyl Additions to Aldehydes
Heaton, Steven B.,Jones, Graham B.
, p. 1693 - 1696 (1992)
The preparation of a rationally designed catalyst system derived from norephedrine is reported.The key stereodirective element emanates from a chromium tricarbonyl group complexed to one face of the aryl ring.The catalysts mediate the addition of diethyl zinc to a variety of aldehydes with extremely high enantioselectivity.Key Words: enantioselective catalyst; norephedrine; arene chromium tricarbonyl; diethyl zinc; chiral 1,2-addition
Enantioselective addition of diethylzinc to aryl aldehydes catalyzed by ADPD imine catalysts
Mino, Takashi,Oishi, Katsuhiko,Yamashita, Masakazu
, p. 965 - 966 (1998)
The use of chiral imines 1-4 prepared from (4S,5S)-(+)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane (ADPD) in the enantioselective addition of diethylzinc to aryl aldehydes is reported. Secondary aryl alcohols are obtained up to 85% ee in good yields.
Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(BINOL) complex
Zhang, Fu-Yao,Yip, Chiu-Wing,Cao, Rong,Chan, Albert S. C.
, p. 585 - 589 (1997)
The enantioselective addition of diethylzine to aldehydes was conveniently achieved by using a catalyst prepared in situ by mixing titanium tetraisopropoxide with S-or R-binaphthol. Optical yields as high as 95.6% were obtained.
Congeners of Troeger's base as chiral ligands
Harmata, Michael,Kahraman, Mehmet
, p. 2875 - 2879 (2000)
(S)-(+)-Troeger's base can be deprotonated and alkylated without loss of stereochemical integrity. An examination of the ability of Troeger's base and several derivatives prepared in this fashion to effect asymmetric induction in the addition of diethylzinc to aromatic aldehydes was conducted. Enantiomeric excesses as high as 86% were achieved, providing evidence that Troeger's base represents a chiral framework which can be modified to produce ligands for catalytic asymmetric synthesis. (C) 2000 Elsevier Science Ltd.
Binaphthyl-based chiral ligands: Design, synthesis and evaluation of their performance in enantioselective addition of diethylzinc to aromatic aldehydes
Yao, Chao,Wu, Piao,Huang, Yue,Chen, Yaoqi,Li, Lin,Li, Yue-Ming
, p. 9712 - 9725 (2020)
The design strategy and the performance of binaphthyl-based chiral ligands were evaluated with computation and enantioselective addition of diethylzinc to aromatic aldehydes. Under optimized conditions, enantioselective addition of diethylzinc to aromatic aldehydes provided the desired optically active secondary alcohols in high isolated yields (up to 91%) and excellent enantiomeric excesses (up to 98% ee).
Asymmetric activation of chiral alkoxyzinc catalysts by chiral nitrogen activators for dialkylzinc addition to aldehydes: Super high-throughput screening of combinatorial libraries of chiral ligands and activators by HPLC-CD/UV and HPLC-OR/RIU systems
Mikami, Koichi,Angelaud, Re?my,Ding, Kuiling,Ishii, Akihiro,Tanaka, Akito,Sawada, Naotaka,Kudo, Kenichi,Senda, Masaaki
, p. 730 - 737 (2001)
Asymmetric catalysts, prepared by chiral ligand exchange or chiral modification, can evolve further into highly activated catalysts through engineering with chiral activators. Two new methodologies for "super high-throughput screening" (SHTS) of chiral ligands and activators have been developed as a combination of HPLC-CD/UV (CD/ UV = circular dichroism/ultraviolet spectroscopy) or -OR/RIU (OR/RIU = optical rotation/refractive index unit) with a combinatorial chemistry (CC) factory. With these techniques, the percent ee of the product is determined within minutes without separation of the enantiomeric products by using a nonchiral stationary phase. Therefore, those SHTS techniques combined with our 'asymmetric activation' concept can provide a powerful strategy for finding the best activated chiral catalyst. ? WILEY-VCH Verlag GmbH, 2001.
Phosphine-free chiral iridium catalysts for asymmetric catalytic hydrogenation of simple ketones
Kumar, Prashant,Irrgang, Torsten,Kostakis, George E.,Kempe, Rhett
, p. 39335 - 39342 (2016)
Novel pyridylalkylamine and aminopyridinato ligand stabilized iridium complexes with no P ligand are introduced. These complexes have been investigated as catalysts for asymmetric hydrogenation of simple ketones, resulting in an active catalyst for bulky alkyl aryl ketones that is α-methylpropiophenone. The ligands were synthesized from inexpensive starting materials and their modular design allows for the introduction of a broad variety of substitution patterns. Additionally, better activity and selectivity was observed at 20 °C and 20 bar H2 pressure with a catalyst loading as low as 0.05 mol% iridium. These phosphorus free catalysts have always been a central issue in both academic and industrial research.
Asymmetric Hydrogenation of Ketones with Polymer-Bound BINAP/Diamine Ruthenium Catalysts
Ohkuma, Takeshi,Takeno, Hiroshi,Honda, Yuji,Noyori, Ryoji
, p. 369 - 375 (2001)
The BINAP/1,2-diphenylethylenediamine RuCl2 complexes bound to a polystyrene resin act as precatalysts for asymmetric hydrogenation of various simple ketones. The enantioselectivity, turnover number, and turnover frequency are comparable to those attained under homogeneous conditions.
Enantioselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral cyclic hydroxyamino ferrocene and chromium complexes: Influence of the complexation on the enantioselectivity
Malfait, Stephane,Pelinski, Lydie,Brocard, Jacques
, p. 2595 - 2610 (1998)
The optically active (arene)chromium complexes (+)-(S, 1S)-7-13, (+)- (S, 1S)-20 and ferrocenyl amino alcohol (+)-(S, 1S)-14-17 were synthesized from enantiomerically pure tricarbonyl(I-indanone)chromium (ee>98), tricarbonyl(1-tetralone)chromium (ee>99) a
Dramatic temperature effect in asymmetric catalysis in the enantioselective addition of diethylzinc to aldehydes
Zhang, Huichang,Chan, Kin Shing
, p. 381 - 382 (1999)
The enantioselectivity of the addition of diethylzinc to aryl aldehydes catalysed by (S)-2-(3-methyl-2-pyridyl)-3,5-di-tert-butylphenol have been found to depend heavily on temperature with the inversion temperatures affected by the para-substituents of a
Ferrocenylseleno amino alcohols as new catalysts for the highly enantioselective alkylation of aldehydes
Fukuzawa,Tsudzuki
, p. 1039 - 1042 (1995)
A chiral or a diastereomeric mixture of 1-[1-(N,N-dimethylaminoethyl)-2-(2'-hydroxyalkylseleno)]ferrocene (DASF) was easily prepared by the chiral diferrocenyldiselenide (1) and epoxides. DASF derivatives efficiently catalyzed the ethylation of aldehydes
Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes
Yang, Xiaowu,Shen, Jianheng,Da, Chaoshan,Wang, Rui,Choi, Michael C. K.,Yang, Liwei,Wong, Kwok-Yin
, p. 133 - 138 (1999)
A series of pyrrolidine derivatives with β-amino alcohol moieties prepared from (S)-proline were found to catalyze the enantioselective addition of diethylzinc to aldehydes to yield optically active secondary alcohols with high enantioselectivities. A mec
Enantioselective hydroboration of olefins catalysed by cationic rhodium complexes of 2-phenylquinazolin-4-yl-2-(diphenylphosphino)naphthalene
McCarthy, Mary,Hooper, Mark W.,Guiry, Patrick J.
, p. 1333 - 1334 (2000)
Cationic rhodium complexes of 2-phenylquinazolin-4-yl-2- (diphenylphosphino)naphthalene catalyse the hydroboration of indene, tetrahydronaphthalene and a range of styrenes in high yields, regioselectivities and with enantiomer excesses of up to 97%.
Dialkylzinc additions with a chiral osmaimidazolidine ligand from asymmetric diamination of olefins
Mu?iz, Kilian
, p. 3547 - 3549 (2003)
A new chiral ligand was prepared in a convenient two-step procedure starting from an asymmetric diamination reaction. Subsequent treatment of the resulting osmaimidazolidine with a phenyl Grignard reagent and titanium tetra(iso-propoxide) furnished a complex that catalyses asymmetric dialkylzinc additions to aromatic aldehydes.
Polystyrene-bound cyclo-BINOLs. New heterogeneous ligands for asymmetric catalysis
Lipshutz,Shin
, p. 9515 - 9521 (2000)
BINOL and substituted BINOLs, which have been tethered between the 7 and 7' sites (i.e. 'cyclo-BINOLs'), can be attached via this linkage to polystyrene resins using a simple acetalization. Efficacy associated with these new ligands is demonstrated in het
Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (S)-2-(N,N-Disubstituted aminomethyl)pyrrolidine
Asami, Masatoshi,Inoue, Seiichi
, p. 1687 - 1690 (1997)
The enantioselective addition of diethylzinc to aldehydes in the presence of a catalytic amount of several chiral diamines, (S)-2-(N,N-disubstituted aminomethyl)pyrrolidines, was studied. Relatively high selectivity was achieved in the case of aromatic al
New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzine to aldehydes
Sola, Lluis,Vidal-Ferran, Anton,Moyano, Albert,Perica, Miquel A.,Riera, Antoni
, p. 1559 - 1568 (1997)
Secondary amines react with (1R,2S)-indene oxide 1 in a completely regioselective manner leading to trans-2-dialkylamino-1-indanols 4a-d in high yield. A Mitsunobu inversion via the corresponding p-nitrobenzoates, followed by reduction with DIBALH leads t
Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof
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Paragraph 0095-0102; 0105-0109, (2021/06/26)
The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.
