210571-76-9Relevant academic research and scientific papers
Facile enantioselective ring-opening reaction of meso epoxides with anilines using (S)-(-)-BINOL-Ti complex as a catalyst
Kureshy, Rukhsana I.,Singh, Surendra,Khan, Noor-Ul H.,Abdi, Sayed H. R.,Suresh, Eringathodi,Jasra, Raksh V.
, p. 1303 - 1309 (2006)
The catalytic enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines was catalyzed by (S)-(-)-BINOL-Ti complexes at ambient temperature to obtain β-amino alcohols in high yield (95%) and enantio-selectivity (ee,
Aminolytic kinetic resolution of trans epoxides for the simultaneous production of chiral trans β-amino alcohols in the presence of chiral Cr(III) salen complex using an ionic liquid as a green reaction media
Kureshy, Rukhsana I.,Kumar, Manish,Agrawal, Santosh,Khan, Noor-ul H.,Abdi, Sayed H.R.,Bajaj, Hari C.
, p. 451 - 456 (2010)
Chiral Cr(III) salen complex 1 having t-Bu substituents at 3,3′ and 5,5′-positions was used as a catalyst for the highly enantioselective aminolytic kinetic resolution (AKR) of racemic trans epoxides with different anilines as nucleophile in the presence
Probing the mechanism of the asymmetric aminolysis of meso-epoxides catalyzed by a proline-based N,N'-dioxide-indium tris(triflate) complex
Gao, Bo,Xie, Mingsheng,Sun, Aimin,Hu, Xiaolei,Ding, Xueqing,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
, p. 1509 - 1518 (2012)
An exploration of the mechanism of the aminolysis of meso-epoxides catalyzed by the proline-based N,N'-dioxide-indium tris(triflate) complex was performed using control experiments, UV-Vis spectroscopy, 1H NMR, electrospray ionization mass spectrometry (ESI-MS) and scanning electron microscopy (SEM). Control experiments disclosed that the ligand-to-indium tris(triflate) ratio, the catalyst loading, the concentration, and the presence of 4 A MS have dramatic effects on this reaction with regard to both the yield and the enantioselectivity. Combined with control experiments, UV-Vis spectroscopy, 1H NMR, ESI-MS and SEM analyses revealed that molecular sieves perform multiple functions in the catalysis. A plausible molecular sieves-assisted reaction pathway was proposed. In this pathway, molecular sieves perform (i) as desiccant to in situ dry the reaction system, (ii) as proton transfer agent to accelerate the catalysis, and (iii) as counter ion source to preserve the electroneutrality of the transition states. Besides, the generality of the substrate scope was further explored; excellent yields (up to 99%) and enantioselectivities (up to 99% ee) were obtained. Copyright
Semi-synthesis of an artificial scandium(iii) enzyme with a β-helical bio-nanotube
Inaba, Hiroshi,Kanamaru, Shuji,Arisaka, Fumio,Kitagawa, Susumu,Ueno, Takafumi
, p. 11424 - 11427 (2012)
We have succeeded in preparing semi-synthesized proteins bound to Sc 3+ ion which can promote an epoxide ring-opening reaction. The Sc3+ binding site was created on the surface of [(gp5βf) 3]2 (N. Yokoi et al.,
Iron(II)-catalyzed enantioselective meso-epoxide-opening with anilines
Plancq, Baptiste,Ollevier, Thierry
, p. 3806 - 3808 (2012)
A highly enantioselective method for the catalytic opening of aromatic meso-epoxides with aniline derivatives was developed. The desired chiral β-amino alcohols were obtained in mostly good to very good yields with excellent enantioselectivities. Structur
Indium-bipyridine catalyzed, enantioselective aminolysis of meso-epoxides
Mai, Enzo,Schneider, Christoph
, p. 2136 - 2138 (2007)
The enantioselective aminolysis of meso-epoxides is efficiently catalyzed by an indium(III)-bipyridine catalyst to furnish highly enantiomerically enriched 1,2-amino alcohols in good yields and up to 98% ee. Georg Thieme Verlag Stuttgart.
Highly Enantioselective Ring-Opening of meso-Epoxides with O- and N-Nucleophiles Catalyzed by a Chiral Sc(III)/bipyridine Complex
Malatinec, ?tefan,Bedná?ová, Eva,Tanaka, Hiroki,Kotora, Martin
supporting information, p. 1249 - 1257 (2021/02/03)
The ring-opening of epoxides is a synthetically significant process widely applied in all kinds of chemistry. Herein, we report the catalytic and highly enantioselective variant of this reaction exploiting our recent endeavors to design and synthesize chi
Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles
Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
, p. 7094 - 7098 (2021/04/16)
A reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant is reported. This protocol represents an unprecedented approach to the chemoselective synthesis of α-hydroxy ketones by electrophile–electrophile cross-coupling.
Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines
Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, (2020/02/04)
A copper-catalyzed enantioselective reductive cross-coupling using aromatic aldehydes and imines, producing chiral β-amino alcohols, is described. The catalytic formation of enantioenriched chiral α-alkoxyalkylcopper(I) species from aromatic aldehydes and the subsequent reaction with imine electrophiles are attractive features of this protocol.
Reductive coupling between aromatic aldehydes and ketones or imines by copper catalysis
Takeda, Mitsutaka,Mitsui, Atsuhisa,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3664 - 3669 (2019/02/14)
The copper-catalyzed reductive coupling of two different carbonyl compounds has been achieved. The reaction of aromatic aldehydes and arylketones with a silylboronate in the presence of a catalytic amount of a CuCl-N-heterocyclic carbene (NHC) complex and a stoichiometric amount of alkoxide base yielded cross-coupled 1,2-diol derivatives. A reaction pathway is proposed that involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species from the aromatic aldehyde and its subsequent coupling with the arylketone. This process was amenable to asymmetric catalysis. This copper catalyst system also enabled the reductive coupling between aromatic aldehydes and imines.
