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.
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.
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.
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
Reich,Cram
, p. 3534,3535 (1969)
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.
An exploration of Suzuki aryl cross coupling chemistry involving [2.2]paracyclophane derivatives
Roche, Alex J.,Canturk, Belgin
, p. 515 - 519 (2005)
Suzuki aryl cross coupling reactions using derivatives of [2.2]paracyclophane were examined. A variety of aryl boronic acids and pinacolate esters were successfully cross coupled with 4-bromo[2.2] paracyclophane under standard Suzuki conditions. Whilst an
Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane
Weinzierl, David,Waser, Mario
, p. 800 - 804 (2021/05/03)
We herein report a method for the kinetic resolution of racemic 4-hydroxy[2.2]paracyclophane by means of a chiral isothiourea-catalyzed acylation with isobutyric anhydride. This protocol allows for a reasonable synthetically useful s-factor of 20 and provides a novel entry to obtain this interesting planar chiral motive in an enantioenriched manner.
