80409-67-2Relevant academic research and scientific papers
Facile synthesis of chiral 2-formyl-1,1′-binaphthyl via lipase-catalyzed acylation and hydrolysis of 1,1′-binaphthyl oximes
Aoyagi, Naoto,Ohwada, Tomoyuki,Izumi, Taeko
, p. 8269 - 8272 (2003)
Lipase-catalyzed acylation of 2-hydroxyiminomethyl-1,1′-binaphthyl [(±)-1] and hydrolysis of 2-acetoxyiminomethyl-1,1′-binaphthyl [(±)-2] yielded optically active oximes 1 and 2 with high enantiomeric excess. Successful synthesis of the optically active aldehyde 4 from chiral O-acetyl oxime 2 occurred without a decrease of enantiomeric excess.
Synthesis of substituted helicenes by Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with alkynes
Kamikawa, Ken,Den, Hiroakira,Tsurusaki, Akihiro,Nagata, Tomoya,Miura, Masahiro
, p. 1069 - 1074 (2018/07/29)
A series of substituted [4] and [5]helicenes were synthesized in moderate to good yields by an Ir-catalyzed annulative coupling of biarylcarboxylic acid chlorides with internal alkynes, which involves facile C-H bond cleavage and decarbonylation. The double annulative coupling of 1, 1′:5′, 1″-ternaphthalene- 2, 2″-dicarboxylic acid dichloride with 4-octyne was also accomplished to give rise to an S-shaped double helicene. Unexpectedly, a π-extended benzofluoranthene-merged [5]- helicene was constructed through the annulative coupling and the successive C(aryl)-C(aryl) bond forming reaction when 1, 1′:4′, 1″-ternaphthalene-2, 2″-dicarboxylic acid dichloride was employed as the substrate. The crystal structure and the optical properties of the latter unique product were also investigated.
Synthesis of a class of binaphthyl monophosphine ligands with a naphthofuran skeleton and their applications in Suzuki-Miyaura coupling reactions
Zhou, Zihong,Liang, Hao,Xia, Wang,Chen, Huixuan,Zhang, Yaqi,He, Xuefeng,Yu, Sifan,Cao, Rihui,Qiu, Liqin
, p. 5967 - 5971 (2018/04/23)
A series of new monophosphine ligands containing a naphthofuran skeleton have been prepared, characterized and evaluated in palladium-catalyzed Suzuki-Miyaura coupling reactions. Using Pd2(dba)3-L6 as the catalyst the reactions were performed with high catalytic activity under mild reaction conditions and the desired coupling products were obtained in good to excellent yields. The new catalyst system also showed broad substrate adaptability and practicality for gram-scale production.
Atroposelective Synthesis of Axially Chiral Biaryls by Palladium-Catalyzed Asymmetric C?H Olefination Enabled by a Transient Chiral Auxiliary
Yao, Qi-Jun,Zhang, Shuo,Zhan, Bei-Bei,Shi, Bing-Feng
supporting information, p. 6617 - 6621 (2017/05/29)
Atroposelective synthesis of axially chiral biaryls by palladium-catalyzed C?H olefination, using tert-leucine as an inexpensive, catalytic, and transient chiral auxiliary, has been realized. This strategy provides a highly efficient and straightforward access to a broad range of enantioenriched biaryls in good yields (up to 98 %) with excellent enantioselectivities (95 to >99 % ee). Kinetic resolution of trisubstituted biaryls bearing sterically more demanding substituents is also operative, thus furnishing the optically active olefinated products with excellent selectivity (95 to >99 % ee, s-factor up to 600).
HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature
Handa, Sachin,Andersson, Martin P.,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
supporting information, p. 4914 - 4918 (2016/04/26)
The new monophosphine ligand HandaPhos has been identified such that when complexed in a 1:1 ratio with Pd(OAc)2, enables Pd-catalyzed cross-couplings to be run using ≤1000 ppm of this pre-catalyst. Applications to Suzuki-Miyaura reactions involving highly funtionalized reaction partners are demonstrated, all run using environmentally benign nanoreactors in water at ambient temperatures.
Organocatalytic atroposelective aldol condensation: Synthesis of axially chiral biaryls by arene formation
Link, Achim,Sparr, Christof
, p. 5458 - 5461 (2014/06/09)
Axially chiral compounds are of significant importance in modern synthetic chemistry and particularly valuable in drug discovery and development. Nonetheless, current approaches for the preparation of pure atropisomers often prove tedious. We demonstrate here a synthetic method that efficiently transfers the stereochemical information of a secondary amine organocatalyst into the axial chirality of tri-ortho-substituted biaryls. An aromatic ring is formed during the dehydration step of the described aldol condensation cascade, leading to highly enantioenriched binaphthyl derivatives. The fundamental course of the reaction is related to the biosynthesis of aromatic polyketides. Head-turning! An organocatalytic atroposelective aldol condensation to tri-ortho-substituted biaryls is described. Key to the process is an efficient transfer of the stereochemical information of a secondary amine catalyst into the axis of chirality of binaphthyl products. The reaction proceeds analogous to the aromatic polyketide biosynthesis and is distinct in its initiation by virtue of dienamine formation. This method allows for the synthesis of axially chiral biaryls with remarkable atroposelectivity of up to e.r. 99:1.
Copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines via 1,4-aminooxygenation of benzene rings
Tnay, Ya Lin,Chen, Cheng,Chua, Yi Yuan,Zhang, Line,Chiba, Shunsuke
supporting information; experimental part, p. 3550 - 3553 (2012/07/30)
A synthetic method of azaspirocyclohexadienones has been developed through copper-catalyzed aerobic spirocyclization of biaryl-N-H-imines prepared by the reaction of biarylcarbonitriles and Grignard reagents.
Efficient chiral monophosphorus ligands for asymmetric Suzuki-Miyaura coupling reactions
Tang, Wenjun,Patel, Nitinchandra D.,Xu, Guangqing,Xu, Xiaobing,Savoie, Jolaine,Ma, Shengli,Hao, Ming-Hong,Keshipeddy, Santosh,Capacci, Andrew G.,Wei, Xudong,Zhang, Yongda,Gao, Joe J.,Li, Wenjie,Rodriguez, Sonia,Lu, Bruce Z.,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 2258 - 2261 (2012/06/30)
A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety in these chiral biaryl products allows facile derivatization for further synthetic applications. A computational study has revealed that a π-π interaction between the two coupling partners can enhance the enantioselectivity of the coupling reaction.
Methodology for the synthesis of 1,2-disubstituted arylnaphthalenes from α-tetralones
Moleele, Simon S.,Michael, Joseph P.,De Koning, Charles B.
, p. 2831 - 2844 (2007/10/03)
α-Tetralones were initially converted into 1-bromo- dihydronaphthalene-2-carbaldehydes and 1-bromo-naphthalene-2-carbaldehydes. These precursors were then subjected to Suzuki coupling reactions to afford 1,2-disubstituted aryldihydronaphthalenes and 1,2-disubstituted arylnaphthalenes, respectively. The former products were oxidized with DDQ to give 1,2-disubstituted arylnaphthalenes.
Synthesis of phenanthrenes and polycyclic heteroarenes by transition-metal catalyzed cycloisomerization reactions
Mamane, Victor,Hannen, Peter,Fuerstner, Alois
, p. 4556 - 4575 (2007/10/03)
Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial π-complexation of the alkyne unit followed by interception of the resulting η2-metal species by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product. Moreover, it is readily extended to the heterocyclic series as exemplified by the preparation of benzoindoles, benzocarbazoles, naphthothiophenes, as well as bridgehead nitrogen heterocycles such as pyrrolo[1,2-a]quinolines. Depending on the chosen catalyst, biaryls bearing halo-alkyne units can either be converted into the corresponding 10-halo-phenanthrenes or into the isomeric 9-halo-phenanthrenes; in the latter case, the concomitant 1,2-halide shift is best explained by assuming a metal vinylidene species as the reactive intermediate. The scope of this novel method for the preparation of polycyclic arenes is illustrated by the total synthesis of a series of polyoxygenated phenanthrenes that are close relatives of the anticancer agent combretastatin A-4, as well as by the total synthesis of the aporphine alkaloid O-methyl-dehydroisopiline and its naturally occurring symmetrical dimer.
