35294-28-1Relevant articles and documents
A chiroptical binaphthopyran switch: Amplified CD response in a polystyrene film
Kickova, Anna,Donovalova, Jana,Kasak, Peter,Putala, Martin
, p. 1109 - 1115 (2010)
Enantiopure 10,10′-bi(naphtho[2,3-b]pyran) (5a) has been prepared from (R)-BINOL by using the attachment of 1,1-diphenylallyl alcohol to positions 3 and 3′ of the binaphthalene via Heck coupling as a key step. The irradiation of 5a in solution with UV lig
Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones
Osakama, Kazuki,Nakajima, Makoto
, p. 236 - 239 (2016)
The enantioselective addition of Grignard reagents to ketones was promoted by a BINOL derivative bearing alkyl chains at the 3,3′-positions. This is the first asymmetric direct aryl Grignard addition to ketones reported to date. A variety of tertiary diaryl alcohols could be obtained in high yields and enantioselectivities without using any other metal source.
Bronsted acid-catalyzed, highly enantioselective addition of enamides to in situ-generated ortho-quinone methides: A domino approach to complex acetamidotetrahydroxanthenes
Saha, Satyajit,Schneider, Christoph
, p. 2348 - 2352 (2015)
The highly enantioselective conjugate addition of enamides and enecarbamates to in situ-generated ortho-quinone methides, upon subsequent N,O-acetalization, gives rise to acetamido-substituted tetrahydroxanthenes with generally excellent enantio- and dias
Enantioselective aryl-aryl coupling facilitated by chiral binuclear gold complexes
Himmelstrup, Jonas,Buendia, Mikkel B.,Sun, Xing-Wen,Kramer, S?ren
, p. 12988 - 12991 (2019)
Herein, we report stoichiometric investigations embodying the first highly enantioselective aryl-aryl coupling facilitated by a gold complex. With up to 91% ee, this is the first demonstration of a transmetalation and C(sp2)-C(sp2) r
Highly efficient synthesis of optically pure 5,5′,6,6′,7, 7′,8,8′-octahydro-1,1′-bi-2-naphthol and -naphthylamine derivatives by partial hydrogenation of 1,1′-binaphthyls with carbon nanofiber supported ruthenium nanoparticles
Takasaki, Mikihiro,Motoyama, Yukihiro,Yoon, Seong-Ho,Mochida, Isao,Nagashima, Hideo
, p. 10291 - 10293 (2007)
(Chemical Equation Presented) Use of Ru/CNF-P, nanoruthenium particles dispersed on a nanocarbon fiber support, realizes highly efficient catalytic partial hydrogenation of 1,1′-bi-2-naphthol and -naphthylamine derivatives. The reactions proceed in high turnover numbers without racemization of the axial chirality, offering a practical procedure for the production of optically pure 5,5′,6,6′,7,7′,8,8′-octahydro-1,1′- binaphthyls in good to high yields.
Tuning the CD spectrum and optical rotation value of a new binaphthalene molecule with two spiropyran units: Mimicking the function of a molecular "AND" logic gate and a new chiral molecular switch
Zhou, Yucheng,Zhang, Deqing,Zhang, Yazhou,Tang, Yalin,Zhu, Daoben
, p. 6164 - 6170 (2005)
With the view to developing new chiral molecular switches and logic gates, a new binaphthalene molecule with two spiropyran units (1) was synthesized and characterized. Absorption and 1H NMR spectral studies of 1 after reaction with acid/base indicate acidichromism can occur to compound 1. The synergistic actions of acid and UV light irradiation result in a remarkable change for the CD spectrum of the relatively dilute solution of 1, mimicking the behavior of a chiral "AND" gate, since the "ouput" is the CD signal. Furthermore, the optical rotation value of the relatively concentrated solution of 1 can be reversibly tuned after sequential reactions with acid and base, and thus a chiral molecular switch with nondestructive "output" signal is realized. The present results not only add a new example of chiral molecular switch with nondestructive readout but also provide a chiral "AND" gate based on the axial chiral binaphthalene to which switchable units are linked.
Design and Development of Axially Chiral Bis(naphthofuran) Luminogens as Fluorescent Probes for Cell Imaging
Jejurkar, Valmik P.,Yashwantrao, Gauravi,Kumar, Pawan,Neekhra, Suditi,Maliekal, Parimal J.,Badani, Purav,Srivastava, Rohit,Saha, Satyajit
, p. 5470 - 5482 (2021/03/03)
Designing chiral AIEgens without aggregation-induced emission (AIE)-active molecules externally tagged to the chiral scaffold remains a long-standing challenge for the scientific community. The inherent aggregation-caused quenching phenomenon associated w
Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
Wang, Sibin,Zhelavskyi, Oleksii,Lee, Jeonghyo,Argüelles, Alonso J.,Khomutnyk, Yaroslav Ya.,Mensah, Enoch,Guo, Hao,Hourani, Rami,Zimmerman, Paul M.,Nagorny, Pavel
supporting information, p. 18592 - 18604 (2021/11/16)
This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll
A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light-Mediated Cycloadditions
Pecho, Franziska,Zou, You-Quan,Gramüller, Johannes,Mori, Tadashi,Huber, Stefan M.,Bauer, Andreas,Gschwind, Ruth M.,Bach, Thorsten
supporting information, p. 5190 - 5194 (2020/04/29)
A chiral phosphoric acid with a 2,2’-binaphthol core was prepared that displays two thioxanthone moieties at the 3,3’-position as light-harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β-carboxyl-substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers
Chen, Song,Chen, Yue-Gang,Gao, Pei-Sen,Liu, Dong,Ma, Hong-Xing,Mei, Tian-Sheng,Qiu, Hui,Shuai, Bin,Wang, Yun-Zhao
supporting information, p. 9872 - 9878 (2020/06/27)
A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.