123750-02-7Relevant academic research and scientific papers
Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates
Barhate, Nivrutti B.,Chen, Chien-Tien
, p. 2529 - 2532 (2002)
(Matrix presented) A series of oxovanadium(IV) complexes derived from tridentate N-ketopinidene-α-amino acids were synthesized. They serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, or 7-substituted 2-naphthols. The best scenario involves the use of a vanadyl complex arising from L-tert-leucine in CCl4. The asymmetric couplings of 2-naphthols can be conducted smoothly at 40-45 °C under a stream of gaseous oxygen, leading to 2,2′dihydroxy-1,1′-binaphthyls in good yields (61-99%) and with enantioselectivities of up to 87%.
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.
Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes
Narute, Sachin,Parnes, Regev,Toste, F. Dean,Pappo, Doron
, p. 16553 - 16560 (2016/12/27)
Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C1- and C2-symmetric BINOLs, in which the 3 and 3′ positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.
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.
Highly selective oxidative cross-coupling of 2-naphthol derivatives with chiral copper(I)-bisoxazoline catalysts
Temma, Tomohisa,Habaue, Shigeki
, p. 5655 - 5657 (2007/10/03)
The asymmetric oxidative coupling reaction of 3-hydroxy-2-naphthoate and 2-naphthol derivatives with the CuCl-(S)-(-)-2,2′-isopropylidenebis(4- phenyl-2-oxazoline) catalyst under an O2 atmosphere was carried out. The reaction proceeded in a highly cross-coupling selective manner (≤99.7%) with a moderate enantioselectivity of up to 65%.
Novel diphosphine compound, production intermediate thereof, transition metal complex containing the compound as ligand and asymmetric hydrogenation catalyst containing the complex
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Page 10-11, (2008/06/13)
The present invention provides a novel phosphine compound, specifically to provide a novel phosphine compound useful as a ligand for the above catalysts, in particular, a novel catalyst having an excellent performance (chemical selectivity, enantio-select
Catalytic enantioselective coupling of 2-naphthols by new chiral oxovanadium complexes bearing a self accelerating functional group
Chu, Chang-Ying,Uang, Biing-Jiun
, p. 53 - 55 (2007/10/03)
New chiral oxovanadium complexes containing an extra phenolic hydroxyl group were found to enhance the catalytic enantioselective coupling of 2-naphthols in moderate to good enantioselectivity.
Novel Achiral Biphenol-Derived Diastereomeric Oxovanadium(IV) Complexes for Highly Enantioselective Oxidative Coupling of 2-Naphthols
Luo, Zhibin,Liu, Quanzhong,Gong, Liuzhu,Cui, Xin,Mi, Aiqiao,Jiang, Yaozhong
, p. 4532 - 4535 (2007/10/03)
Chiral binaphthols 3 were obtained by oxidative coupling of 2-naphthols in the presence of achiral biphenol-derived diastereomeric VIV oxo complexes. Despite its conformationally flexible biphenyl moiety, the best catalyst 2 (90-97 percent ee, 62-99 percent yield) exhibits comparable or even higher enantioselectvities than an analogue with an optically pure 1,1'-binaphthyl group.
C2-symmetric bisphosphine ligands derived from 1,1- binaphthyldiamines and diphenylphosphinobenzoic acid for palladium catalyzed desymmetrizations
Lim, Chung Woo,Lee, Sang-gi
, p. 5131 - 5136 (2007/10/03)
A series of novel C2-symmetric bisphosphine ligands derived from DPPBA and C2-symmetric 1,1' -binaphthyldiamines has been synthesized. In palladium catalyzed desymmetrization of meso cyclic carbamates, the enantioselectivity and the stereochemistry of the major enantiomers are largely affected by the substitution position of DPPBA moiety on the 1,1'-binaphthyl chiral scaffold. (C) 2000 Elsevier Science Ltd.
Molecular recognition of pyranosides by a family of trimeric, 1,1'- binaphthalene-derived cyclophane receptors
Baehr, Anja,Droz, Anne Sophie,Puentener, Martin,Neidlein, Ulf,Anderson, Sally,Seiler, Paul,Diederich, Francois
, p. 1931 - 1963 (2007/10/03)
The synthesis and carbohydrate-recognition properties of a new family of optically active cyclophane receptors, 1-3, in which three 1,1'- binaphthalene-2,2'-diol spacers are interconnected by three buta-1,3- diynediyl linkers, are described. The macrocycles all contain highly preorganized cavities lined with six convergent OH groups for H-bonding and complementary in size and shape to monosaccharides. Compounds 1-3 differ by the functionality attached to the major groove of the 1,1'-binaphthalene- 2,2'-diol spacers. The major grooves of the spacers in 2 are unsubstituted, whereas those in 1 bear benzyloxy (BnO) groups in the 7,7'-positions and those in 3 2-phenylethyl groups in the 6,6'-positions. The preparation of the more planar, D3-symmetrical receptors (R,R,R)-1 (Schemes 1 and 2), (S,S,S)- 1 (Scheme 4), (S,S,S)-2 (Scheme 5), and (S,S,S)-3 (Scheme 8) involved as key step the Glaser-Hay cyclotrimerization of the corresponding OH-protected 3,3'-diethynyl-1-1'-binaphthalene-2,2'-diol precursors, which yielded tetrameric and pentameric macrocycles in addition to the desired trimeric compounds. The synthesis of the less planar, C2-symmetrical receptors (R,R,S)-2 (Scheme 6) and (S,S,R)-3 (Scheme 9) proceeded via two Glaser-Hay coupling steps. First, two monomeric precursors of identical configuration were oxidatively coupled to give a dimeric intermediate which was then subjected to macrocyclization with a third monomeric 1,1'-binaphthalene precursor of opposite configuration. The 3,3'-dialkynylation of the OH- protected 1,1'-binaphthalene-2,2'-diol precursors for the macrocyclizations was either performed by Stille (Scheme 1) or by Sonogashira (Schemes 4, 5, and 8) cross-coupling reactions. The flat D3-symmetrical receptors (R,R,R)- 1 and (S,S,S)-1 formed 1:1 cavity inclusion complexes with octyl 1-O- pyranosides in CDCl3 (300 K) with moderate stability (ΔG0 ca. -3 kcal mol-1) as well as moderate diastereo(Δ(ΔG0) up to 0.7 kcal mol-1) and enantioselectivity (Δ(ΔG0) =0.4 kcal mol-1) (Table 1). Stoichiometric 1:1 complexation by (S,S,S)-2 and (S,S,S)-3 could not be investigated by 1H- NMR binding titrations, due to very strong signal broadening. This broadening of the 1H-NMR resonances is presumably indicative of higher-order associations, in which the planar macrocycles sandwich the carbohydrate guests. The less planar C2-symmetrical receptor (S,S,R)-3 formed stable 1:1 complexes with binding free enthalpies of up to ΔG0 = - 5.0 kcal mol-1 (Table 2). With diastereoselectivities up to Δ(ΔG0) = 1.3 kcal mol-1 and enantioselectivities of Δ(ΔG0)= 0.9 kcal mol-1, (S,S,R)-3 is among the most selective artificial carbohydrate receptors known.
