118495-07-1Relevant academic research and scientific papers
Enantioselective iron/bisquinolyldiamine ligand‐catalyzed oxidative coupling reaction of 2‐naphthols
Liu, Wen-Bo,Usman, Muhammad,Wu, Lin-Yang
, (2020/02/25)
An iron‐catalyzed asymmetric oxidative homo‐coupling of 2‐naphthols for the synthesis of 1,1′‐Bi‐2‐naphthol (BINOL) derivatives is reported. The coupling reaction provides enantioenriched BINOLs in good yields (up to 99%) and moderate enantioselectivities (up to 81:19 er) using an iron‐complex generated in situ from Fe(ClO4)2 and a bisquinolyldiamine ligand [(1R,2R)‐N1,N2‐di(quinolin‐8‐yl)cyclohexane‐1,2‐diamine, L1]. A number of ligands (L2–L8) and the analogs of L1, with various substituents and chiral backbones, were synthesized and examined in the oxidative coupling reactions.
Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols
Chen, Ye-Hui,Li, Heng-Hui,Li, Shaoyu,Tan, Bin,Xiang, Shao-Hua,Zhang, Xiao
, p. 11374 - 11378 (2020/05/25)
Presented here is a class of novel axially chiral aryl-p-quinones as platform molecules for the preparation of non-C2 symmetric biaryldiols. Two sets of aryl-p-quinone frameworks were synthesized with remarkable enantiocontrol by means of chiral phosphoric acid catalyzed enantioselective arylation of p-quinones by central-to-axial chirality conversion. These aryl-p-quinones were then used to access a wide spectrum of highly functionalized non-C2 symmetric biaryldiols with excellent retention of the enantiopurity.
Lewis Acid-Mediated Cyanation of Phenols Using N-Cyano-N-phenyl-p-toluenesulfonamide
Zhang, Wu,Li, Tao,Wang, Qingli,Zhao, Wanxiang
supporting information, p. 4914 - 4918 (2019/11/03)
Lewis acid-mediated cyanation of phenol derivatives with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has been developed. The reaction proceeded efficiently with high regioselectivity to produce aromatic nitriles in moderate to excellent yields, which provides a direct and practical access to valuable products. (Figure presented.).
Unsymmetrical banana-shaped liquid crystalline compounds derived from 2,7-dihydroxynaphthalene
Simion, Aurel,Huzum, Cosmin-Constantin,Carlescu, Irina,Lisa, Gabriela,Balan, Mihaela,Scutaru, Dan
, p. 673 - 683 (2015/08/24)
The synthesis and characterization of new asymmetric bent-core compounds derived from 2,7-dihydroxynaphthalene with various connecting groups between the aromatic rings and alkyloxy terminal substituents at the end of the long arm are presented. Some 1,4-disubstituted phenylene rings with an azo or ester linkage between them have been used as calamitic pro-mesogen units. The synthetic strategies to obtain the final esteric derivatives involved the esterification of 7-(benzyloxy)naphthalen-2-ol with 4-((4-(alkyloxy)phenyl)-azo)benzoyl chlorides or with 4-((4-(alkyloxy)benzoyl)oxy)benzoic acids in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). The mesomorphic properties were assigned by optical polarizing microscopy and differential scanning calorimetry. All the compounds showed mesomorphic properties of the enantiotropic or monotropic type, the liquid crystalline behavior depending on the linking group between the phenylene rings. Thermogravimetric studies evidenced that all compounds were stable in the range of the existence of mesophases.
Regioselective O-alkylations and acylations of polyphenolic substrates using a calix[4]pyrrole derivative
Cafeo, Grazia,Kohnke, Franz H.,Valenti, Luca
experimental part, p. 4138 - 4140 (2009/12/06)
The 10α,20α-bis(4-nitrophenyl)-calix[4]pyrrole 2 can act as a topologically selective protecting group in the O-alkylation and acylation of polyphenolic polycyclic aromatic compounds thanks to the regioselective formation of phenolate-type complexes. Rema
A novel molecular cleft based on dioxocin ring, part I: Synthesis and conformational analysis
Vafakish, Bahareh,Rashidi-Ranjbar, Parviz
experimental part, p. 2741 - 2753 (2010/04/25)
The Molecular cleft 1 using 8-methyl-16H-dinaphtho[2,1-d:1,2-g][1,3]dioxocin-2,14-diol as a spacer was synthesized. Density functional calculations at B3LYP/6-31G level of theory indicates that 8-methyl-16H-dinaphtho[2,1-d:1,2-g][1,3]dioxocin, the central
Linker-oriented design of binaphthol derivatives for optical resolution using lipase-catalyzed reaction
Taniguchi, Tomohiro,Fukuba, Taka-Aki,Nakatsuka, Shuhei,Hayase, Shuichi,Kawatsura, Motoi,Uno, Hidemitsu,Itoh, Toshiyuki
, p. 3875 - 3884 (2008/09/20)
(Chemical Equation Presented) Candida antarctica lipase B (CAL-B) is one the most frequently used enzymes in organic synthesis for the preparation of optically active alcohols. However, it has not been used for the optical resolution of (±)-2,2′-binaphthol. We established an efficient linker-oriented design of 2,2′-binaphthol derivatives that is appropriate for optical resolution using CAL-B-catalyzed hydrolysis reaction. Methyl 4-(1-(6-bromo-2-methoxymethoxynaphthalen-1-yl)-6-bromonaphthalen-2-yloxy) butanoate was hydrolyzed by CAL-B to afford a corresponding acid with excellent enantioselectivity (E > 200). Two types of optically active binaphthol derivatives, 1-(2-hydroxy-6-(naphthalen-1-yl)naphthalen-1-yl)-6-(naphthalen-1- yl)naphthalen-2-ol and 6-butyl-1-(6-butyl-2-hydroxynaphthalen-1-yl)naphthalen-2- ol, were prepared by this chemoenzymatic reaction protocol and were used as chiral templates for symmetric reactions.
1-ALKYNYL-2-ARYLOXYALKYLAMIDES AND THEIR USE AS FUNGICIDES
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Page/Page column 41, (2008/06/13)
Compounds of the formula wherein the substituents are as defined in the claims, are useful as fungicides.
Liquid crystalline properties of unsymmetrical bent-core compounds containing chiral moieties
Reddy, R. Amaranatha,Sadashiva,Baumeister
, p. 3303 - 3316 (2007/10/03)
The synthesis, characterization and mesomorphic properties of new unsymmetrical bent-core compounds containing chiral moieties are reported. These compounds have been derived from either 3-hydroxybenzoic acid or 2,7-dihydroxynaphthalene as the central unit. The chiral group is incorporated either within the bent-core structure as a linking group or is appended in the terminal position. The influence of the position of the chiral moiety on the mesomorphic properties has been investigated. The bent-core compounds containing a chiral group (octan-2-ol) in the terminal chain exhibit a direct transition from chiral calamitic phases such as SmC*, SmC*γ to a polar banana phase with a two-dimensional lattice (ColobP A*) on decreasing temperature. In order to prove this phase sequence, the corresponding compound with a racemic octan-2-ol group at the terminal chain has been synthesized. The preliminary observations and investigations are presented for comparison with the chiral compound. Possible explanations for this unusual phase sequence and the models for the Col obPA* (SmCsPA*) phase are also discussed on the basis of X-ray and electric field experiments. The Royal Society of Chemistry 2005.
A modular route to nonracemic cyclo-NOBINs. Preparation of the parent ligand for homo- and heterogeneous catalysis
Lipshutz, Bruce H.,Buzard,Olsson, Christina,Noson, Kevin
, p. 4443 - 4449 (2007/10/03)
A sequence which combines a nonracemic tether, a naphthyl diol, and an aminonaphthol has been developed leading to the new ligand cyclo-NOBIN, which can easily be mounted onto polystyrene. Opportunities for extending the route to substituted cyclo-NOBINs are also discussed.
