18531-91-4Relevant articles and documents
A New Catalytic System for Aerobic Oxidative Coupling of 2-Naphthol Derivatives by the Use of CuCl-Amine Complex: A Practical Synthesis of Binaphthol Derivatives
Noji, Masahiro,Nakajima, Makoto,Koga, Kenji
, p. 7983 - 7984 (1994)
Aerobic oxidative coupling of 2-naphthol derivatives by the use of 1 molpercent of CuCl-amine complex afforded binaphthol derivatives in excellent yields.
Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine ligand
Kim, Kyoung Hoon,Lee, Dae-Woong,Lee, You-Sang,Ko, Dong-Hyun,Ha, Deok-Chan
, p. 9037 - 9042 (2004)
Mono-N-alkylated octahydrobinaphthyl-2,2′-diamine (H 8-BINAM) chiral ligands were employed in the catalytic and asymmetric oxidative coupling of methyl 3-hydroxy-2-naphthoate to the corresponding binaphthol derivative. The diamine ligand with one N-(3-pentyl) group shows highest enantioselectivity in the biaryl coupling among other BINAM derivatives, and the coupling reaction proceeds faster than the reactions using alkanediamine ligands.
Efficient Oxidative Coupling of 2-Naphthols Catalyzed by Alumina-Supported Copper(II) Sulfate Using Dioxygen as Oxidant
Sakamoto, Takaaki,Yonehara, Hisatomo,Pac, Chyongjin
, p. 6859 - 6861 (1994)
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Horseradish peroxidase: An effective but unselective biocatalyst for biaryl synthesis
Schmitt, Marko M.,Schueler, Ellen,Braun, Myriam,Haering, Dietmar,Schreier, Peter
, p. 2945 - 2946 (1998)
The oxidative dimerization of phenolic and naphtholic compounds catalyzed by horseradish peroxidase was investigated. Contrary to Sridhar et al. [Tetrahedron Lett., 1997, 38, 5695-5696] exclusively racemic biaryl compounds were identified.
In-depth structure-selectivity investigations on asymmetric, copper-catalyzed oxidative biaryl coupling in the presence of 5-cis-substituted prolinamines
Prause, Felix,Arensmeyer, Benjamin,Fr?hlich, Benjamin,Breuning, Matthias
, p. 2215 - 2226 (2015)
Thirteen new and 25 known prolinamines carrying an additional 5-cis substituent were evaluated as the chiral ligands in asymmetric copper-catalyzed, oxidative biaryl coupling of 3-hydroxy-2-naphthoates. Comprehensive structure-selectivity investigations r
Resolution of (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid using (1R,2R)-trans-cyclohexane-1,2-diamine
Someshwar, Nagamalla,Ramanathan, Chinnasamy Ramaraj
, p. 1209 - 1213 (2015)
A simple and efficient method has been developed to resolve (±)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarboxylic acid [(±)-BINOL-3,3′-dicarboxylic acid] (±)-1 using inexpensive and readily accessible chiral resolving agent (1R,2R)-trans-cyclohexane-1,2-diamine 2. Enantiomers of BINOL-3,3′-dicarboxylic acid were obtained in good yields and enantiomeric purity, for example, (S)-(-)-1 was isolated in 34% yield with >99% ee and (R)-(+)-1 was obtained in 36% yield with >99% ee. The formation of diastereomeric salt A between (S)-BINOL-3,3′-dicarboxylic acid and (1R,2R)-trans-cyclohexane-1,2-diamine was ascertained by using IR, single crystal X-ray crystallography, and HRMS.
Microwave-assisted efficient oxidative coupling of 2-naphthols in the solid state
Ji, Shun-Jun,Lu, Jianmei,Zhu, Xinlin,Yang, Jin,Lang, Jian-Ping,Wu, Lin
, p. 3069 - 3074 (2002)
Microwave-assisted oxidative coupling of 2-naphthols at solid state gave the corresponding coupling products in high yields, which provides a simple, rapid and efficient approach to the preparation of binaphthols.
Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling
Zhao, Xiao-Jing,Li, Zi-Hao,Ding, Tong-Mei,Tian, Jin-Miao,Tu, Yong-Qiang,Wang, Ai-Fang,Xie, Yu-Yang
, p. 7061 - 7065 (2021/02/27)
A challenging direct asymmetric catalytic aerobic oxidative cross-coupling of 2-naphthylamine and 2-naphthol, using a novel CuI/SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′-disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF3 of L17 and H-1,8 of 2-naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross-coupling reaction.
Isothiourea-Catalysed Regioselective Acylative Kinetic Resolution of Axially Chiral Biaryl Diols
Qu, Shen,Greenhalgh, Mark D.,Smith, Andrew D.
supporting information, p. 2816 - 2823 (2019/02/05)
An operationally simple isothiourea-catalysed acylative kinetic resolution of unprotected 1,1′-biaryl-2,2′-diol derivatives has been developed to allow access to axially chiral compounds in highly enantioenriched form (s values up to 190). Investigation of the reaction scope and limitations provided three key observations: i) the diol motif of the substrate was essential for good conversion and high s values; ii) the use of an α,α-disubstituted mixed anhydride (2,2-diphenylacetic pivalic anhydride) was critical to minimize diacylation and give high selectivity; iii) the presence of substituents in the 3,3′-positions of the diol hindered effective acylation. This final observation was exploited for the highly regioselective acylative kinetic resolution of unsymmetrical biaryl diol substrates bearing a single 3-substituent. Based on the key observations identified, acylation transition state models have been proposed to explain the atropselectivity of this kinetic resolution.
