157018-15-0Relevant articles and documents
Highly Efficient Kinetic Resolution of PHANOL by Chiral Phosphoric Acid Catalyzed Asymmetric Acylation
Mori, Keiji,Kishi, Hiroki,Akiyama, Takahiko
, p. 365 - 370 (2017)
We report herein a highly efficient kinetic resolution of PHANOL by chiral phosphoric acid catalyzed asymmetric acylation. PHANOL enantiomers were well differentiated by the chiral environment of chiral phosphoric acid, and both the corresponding monoester and PHANOL were obtained with excellent enantioselectivities (98% ee and 92% ee, respectively). Detailed examination of the substrates suggests that the presence of two hydroxy groups in PHANOL was critical for both reactivity and enantioselectivity.
Development of Planar Chiral Iodoarenes Based on [2.2]Paracyclophane and Their Application in Catalytic Enantioselective Fluorination of β-Ketoesters
Wang, Yang,Yuan, Hang,Lu, Hongfei,Zheng, Wen-Hua
, p. 2555 - 2558 (2018)
The design and synthesis of novel planar chiral iodoarenes based on [2.2]paracyclophane is reported. A process of highly enantioselective oxidative fluorination of a β-ketoester with 3HF-Et3N as a nucleophilic fluoride source mediated by these new hypervalent iodine catalysts has been developed. This represents the first highly enantioselective reaction catalyzed by planar chiral hypervalent iodine.
Improved synthesis of enantiopure 4-hydroxy[2.2]paracyclophane
Friedmann, Christian J.,Ay, Sefer,Braese, Stefan
, p. 4612 - 4614 (2010)
(Figure presented) 4-Hydroxy[2.2]paracyclophane is readily prepared via an improved synthetic protocol from unsubstituted [2.2]paracyclophane. The key step is a Dakin oxidation of 4-formyl[2.2]paracyclophane. This allows a rapid access to large quantities of the product and an easy synthesis of the enantiopure form.
3D Coumarin Systems Based on [2.2]Paracyclophane: Synthesis, Spectroscopic Characterization, and Chiroptical Properties
Delcourt, Marie-Léonie,Reynaud, Corentin,Turcaud, Serge,Favereau, Ludovic,Crassous, Jeanne,Micouin, Laurent,Benedetti, Erica
, p. 888 - 899 (2019)
In this article, we report the preparation of a series of [2.2]paracyclophane-fused coumarin systems through a simple and general procedure involving a transition-metal-catalyzed cyclization of aryl alkynoates as the key step. We also highlight the influence of the [2.2]paracyclophane (pCp) motif and its "phane" interactions on the spectroscopic properties of the newly synthesized fluorophores, which emit in the blue-green region of the visible spectrum (?em up to 560 nm) and show extremely large Stokes shifts (up to 230 nm). Finally, we demonstrate that our straightforward approach can easily be used to access optically active planar chiral 3D coumarins. Compared to previously described fluorescent paracyclophanes and other organic dyes, our compact heteroaromatic derivatives show promising chiroptical properties, both in term of circular dichroism (gabs 8 × 10 -3) and circularly polarized luminescence (glum 5 × 10 -3), thus demonstrating a practical application of our synthetic method.
Planar-chiral building blocks for metal-organic frameworks
Cakici, Murat,Gu, Zhi-Gang,Nieger, Martin,Bürck, Jochen,Heinke, Lars,Br?se, Stefan
, p. 4796 - 4798 (2015)
The first example of a planar-chiral building block being used for chiral metal-organic frameworks (MOFs) is presented. The porous MOF structure combined with the chiral properties of the planar linker allows a selective adsorption, demonstrated for a nonpolar terpene limonene in thin surface-mounted MOF films.
Enzymatic kinetic resolution of (±)-4-acetoxy[2.2] paracyclophane by candida cylindracea lipase. An efficient route for the preparation of(+)-R-4-Hydroxy- and (+)-S-4-acetoxy[2.2)paracyclophane
Cipiciani, Antonio,Fringuelli, Francesco,Mancini, Vittorio,Piermatti, Oriana,Scappini, Anna Maria,Ruzziconi, Renzo
, p. 11853 - 11858 (1997)
The enzymatic kinetic resolution of (±)-4-acetoxy[2.2]paracyclophane by Candida cylindracea lipase was investigated in water and in a two-phase aqueous organic system. The (+)-(R)4-hydroxy- and (c)-(S)-4-acetoxy[2,2]-paracyclophanes were isolated in excellent yields and high enantiomeric excesses. The resolution was carried out on multi-gram scale in hexane-water at 40°C.
Photochromism of novel chromenes constrained to be part of [2.2]paracyclophane: Remarkable 'phane' effects on the colored o-quinonoid intermediates
Moorthy, Jarugu Narasimha,Mandal, Susovan,Kumar, Amrit
, p. 82 - 88 (2013)
The photochemistry of rationally designed chromenes that are constrained to be part of [2.2]paracyclophane, i.e., CP-H and CP-OMe, was investigated to examine the effect of through-space delocalization in the cyclophane core (phane effect) on the photochr
Synthesis of planar chiral [2.2]paracyclophane monophosphine ligands and their application in the umpolung allylation of aldehydes
Zhang, Tang-Zhi,Dai, Li-Xin,Hou, Xue-Long
, p. 251 - 259 (2007)
Chiral [2.2]paracyclophane monophosphines 8 were synthesized via resolution using chiral palladacycle 10. Chiral phosphinite 5 was also prepared from 4-hydroxy[2.2]paracyclophane. Phosphines 8 and phosphinite 5 were used as the ligand in the umpolung ally
Synthesis of bis(benzoxazole) frameworks chiralized by planar chiral [2.2]Paracyclophane
Polat, Emrah,Turbedaroglu, Ozge,Cakici, Murat
, (2021)
In this study, a new class of chiral bis(benzoxazole) has been synthesized. The bis(benzoxazole) framework, which has an achiral structure was chiralized by a planar chiral [2.2]paracyclophane moiety. Both enantiomeric forms of the bis(benzoxazole) deriva
Influence of pH and temperature on the enantioselectivity of propan-2-ol-treated Candida rugosa lipase in the kinetic resolution of (±)-4-acetoxy-[2,2]-paracyclophane
Cipiciani, Antonio,Bellezza, Francesca,Fringuelli, Francesco,Silvestrini, Maria Grazia
, p. 2277 - 2281 (2001)
The reaction temperature, pH of the aqueous medium and use of an aqueous-n-hexane reaction medium markedly influenced the hydrolysis rate and enantioselectivity of (±)-4-acetoxy-[2,2]-paracyclophane with propan-2-ol-treated Candida rugosa lipase. The results have been justified on the basis of a possible conformational change in the enzyme as a consequence of the displacement of its polypeptide lid.
