114091-67-7Relevant academic research and scientific papers
Heterogeneous asymmetric catalysis with homochiral metal-organic frameworks: Network-structure-dependent catalytic activity
Wu, Chuan-De,Lin, Wenbin
, p. 1075 - 1078 (2007)
It's all in the preparation: Heterogeneous asymmetric catalysts based on two homochiral highly porous metal-organic frameworks formed from the same building blocks show remarkably different activity. Although both catalysts are based on twofold interpenetrated structures, one catalyzes the addition of diethylzinc to aromatic aldehydes with high enantioselectivity (up to 90% ee), while the other is inactive. (Chemical Equation Presented).
Regioselective substitution of fluorine in F8BINOL as a versatile route to new ligands with axial chirality
Chen, Yu,Yekta, Shahla,Martyn, L. James P.,Zheng, Juan,Yudin, Andrei K.
, p. 3433 - 3436 (2000)
(Equation Presented) Nucleophilic substitution of aromatic fluorine in F8BINOL offers the possibility of selectively introducing a variety of substituents at the 6, 6′, 7, and 7′ positions. The configurational integrity of the homochiral precur
Copper(I)-Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant-by-Quadrant Structure Modification of Chiral Bisphosphine Ligands
Iwamoto, Hiroaki,Endo, Kohei,Ozawa, Yu,Watanabe, Yuta,Kubota, Koji,Imamoto, Tsuneo,Ito, Hajime
, p. 11112 - 11117 (2019)
The first copper(I)-catalyzed enantioselective borylation of racemic benzyl chlorides has been realized by a quadrant-by-quadrant structure modulation of QuinoxP*-type bisphosphine ligands. This reaction converts racemic mixtures of secondary benzyl chlorides into the corresponding chiral benzylboronates with high enantioselectivity (up to 92 % ee). The results of mechanistic studies suggest the formation of a benzylic radical intermediate. The results of DFT calculations indicate that the optimal bisphosphine-copper(I) catalyst engages in noncovalent interactions that efficiently recognize the radical intermediate, and leads to high levels of enantioselectivity.
Chiral C2-symmetric ligands containing two binaphthyl units linked by 2,2′-bipyridyl bridge in asymmetric catalysis
Bai, Xiao-Li,Kang, Chuan-Qing,Liu, Xu-Dong,Gao, Lian-Xun
, p. 727 - 731 (2005)
The catalytic activities of new chiral C2-symmetric ligands 1-4 in the asymmetric alkylation of aromatic aldehydes with diethylzinc to give 1-arylpropanols are studied. In most cases, the yields were good and enantioselectivities up to 87% were
Nickel-Catalyzed Ring-Opening C-O Functionalization of peri-Xanthenoxanthenes for 8-Substituted Binaphthol Synthesis
Matsuyama, Naoki,Minamino, Naoto,Shimada, Toyoshi,Kamei, Toshiyuki
, p. 3908 - 3912 (2021)
Herein, we disclose the Ni-catalyzed ring-opening C-O functionalization of peri-xanthenoxanthenes using Grignard reagents that forms 8-monofunctionalized binaphthols. 1,2-Bis(dicyclohexylphosphino)ethane was the best ligand for alkylations and ICy for arylation. After mechanistic investigations, we assumed that the reaction proceeds via C-O reduction and subsequent C-O functionalization. To verify the mechanism, the intermediate after reduction was isolated. Moreover, the asymmetric addition, using 8-octylbinaphthol after optical resolution, was studied.
Easily accessible chiral imidazolinium salts bearing two hydroxy-containing substituents as shift reagents and carbene precursors
Jurcik, Vaclav,Gilani, Mazhar,Wilhelm, Rene
, p. 5103 - 5109 (2006)
The behavior of new enantiopure imidazolinium salts bearing two hydroxy-containing substituents as chiral shift reagents and as carbene precursors for diethylzinc addition to aldehydes is presented. The new hydroxy-containing imidazolinium salts can be prepared in a few steps from amino alcohols and qualify as new tridentate ligands and ionic liquids. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
A new class of C2 chiral photodimer ligands for catalytic enantioselective diethylzinc addition to arylaldehydes
Ueda, Yuki,Yagishita, Fumitoshi,Ishikawa, Hiroki,Kaji, Yuki,Baba, Nozomi,Kasashima, Yoshio,Mino, Takashi,Sakamoto, Masami
, p. 6254 - 6258 (2015)
Abstract A new class of C2 chiral materials was easily prepared by the photodimerization reaction of (R)-N-phenethyl-2-chromonecarboxamide followed by recrystallization. Reduction of the photodimer gave the corresponding alcohol stereoselectively. Both C2 chiral materials worked effectively as ligands for enantioselective ethylation of arylaldehydes using diethylzinc.
Efficient chirality switching in the addition of diethylzinc to aldehydes in the presence of simple chiral α-amino amides
Burguete, M. Isabel,Collado, Manuel,Escorihuela, Jorge,Luis, Santiago V.
, p. 9002 - 9005 (2007)
(Chemical Equation Presented) It works both ways: A very simple and efficient dual enantioselective control in the addition of diethylzinc to benzaldehyde can be achieved by using nickel complexes of chiral α-amino amide derivatives. Whereas complexes with 1:1 stoichiometries afford the S alcohol as the major enantiomer, 1:2 (metal/ligand) complexes lead to the predominant formation of the R enantiomer (see scheme).
A homochiral porous metal-organic framework for highly enantioselective heterogeneous asymmetric catalysis
Wu, Chuan-De,Hu, Aiguo,Zhang, Lin,Lin, Wenbin
, p. 8940 - 8941 (2005)
A homochiral porous noninterpenetrating metal-organic framework (MOF), 1, was constructed by linking infinite 1D [Cd(μ-Cl)2]n zigzag chains with axially chiral bipyridine bridging ligands containing orthogonal secondary functional groups. The secondary ch
PQXdpap: Helical Poly(quinoxaline-2,3-diyl)s Bearing 4-(Dipropylamino)pyridin-3-yl Pendants as Chirality-Switchable Nucleophilic Catalysts for the Kinetic Resolution of Secondary Alcohols
Murakami, Ryo,Suginome, Michinori,Yamamoto, Takeshi
supporting information, p. 8711 - 8716 (2021/11/24)
Helically chiral poly(quinoxaline-2,3-diyl)s bearing 4-(dipropylamino)pyridin-3-yl pendants at the 5-position of the quinoxaline ring (PQXdpap) exhibited high catalytic activities and moderate to high selectivities (up to s = 87) in the acylative kinetic resolution of secondary alcohols. The solvent-dependent helical chirality switching of PQXdpap between pure toluene and a 1:1 mixture of toluene and 1,1,2-trichloroethane enabled the preparation of either compound of a pair of enantiomerically pure alcohols (>99% ee) from a single catalyst.
