A highly stereoselective synthesis of s(-)-[1,1′-binaphthalene]-2,2′-diol

Brussee, Johannes; Jansen, A. C. A.

doi:10.1016/s0040-4039(00)88151-4

Cited by 108 publications

(44 citation statements)

References 11 publications

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“…C hiral 1,4-diols such as TADDOLs [1,2] or BINOLs [3], often used as ligands for transition metal catalysed asymmetric synthesis, show a great structural diversity, still preserving the catalytic functionality. They have hindered structures containing two adjacent stereocenters, resulting in a fixed angle between the metal-complexing hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

Structural analysis of sterically hindered 1,4‐diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study

Sandberg

Brusentsev

Eklund

et al. 2011

Int J of Quantum Chemistry

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ABSTRACT:The structures of TADDOL-like α-conidendrin-based chiral 1,4-diols (LIGNOLs) have been studied at molecular mechanics, Hartree-Fock (HF)/6-31G* and DFT/B3LYP/TZVP level of theory. The molecules included were 1,1-diphenyl, two diastereomers of 1,1,4-triphenyl, 1,1,4,4-tetraphenyl, and 1,1,4,4-tetramethyl 1,4-diol. Several conformers of each molecule were studied thorougly also including the entropy contributions. For the triphenyl 1,4-diols, which can form π − π interactions between phenyl rings, the DFT optimized structures differed significantly from the HF optimized ones. A property for the most stable structures, in addition to the ability to form π − π interactions, seemed to be the possibility to have the aliphatic six-membered ring in a boat conformation. For all of the studied LIGNOLs some conformers were found, where the two OH groups pointed almost to the same direction. By this an intramolecular hydrogen bond can be formed between them. The bridging hydrogen atom falls at the same place as a chelate-bonded metal ion would be situated, as in the case of the analogous molecules, TADDOLs, but only a few of these molecules would be able to work well as ligands for asymmetric catalysis.

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Section: Introductionmentioning

confidence: 99%

Structural analysis of sterically hindered 1,4‐diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study

Sandberg

Brusentsev

Eklund

et al. 2011

Int J of Quantum Chemistry

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“…[3] Existing catalysts for the asymmetric preparation of chiral binaphthols include copper complexes of chiral amines or their derivatives [4] and chiral V IV O complexes with either one or two stereogenic metal centers.[5] Recently, dimeric copper(ii) complexes [4b,e,f] or dinuclear V IV O complexes [5d,e] have been shown to be better catalysts with a high enantioselectivity. In the above reports, the catalytic metal complexes were prepared in situ by reacting a chiral ligand with a desired metal ion (Cu I , Cu II , or V IV O).…”

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confidence: 99%

Structurally Defined Catalysts for Enantioselective Oxidative Coupling Reactions

2003

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+Pure binaphthol enantiomers and their derivatives are important chiral ligands for a wide range of asymmetric syntheses.[1] The facile conversion of binaphthol into 2,2'-(diphenylphosphanyl)-1,1'-binaphthyl (BINAP) is particularly noteworthy because BINAP greatly expanded the synthetic utilities of binaphthol in asymmetric catalysis.[2] In light of the wide-ranging and important applications of these compounds, catalytic asymmetric preparation of chiral binaphthols and improvements in the enantioselectivity of the associated catalysts have continued to attract the attention of many researchers. [3] Existing catalysts for the asymmetric preparation of chiral binaphthols include copper complexes of chiral amines or their derivatives [4] and chiral V IV O complexes with either one or two stereogenic metal centers.[5] Recently, dimeric copper(ii) complexes [4b,e,f] or dinuclear V IV O complexes [5d,e] have been shown to be better catalysts with a high enantioselectivity. In the above reports, the catalytic metal complexes were prepared in situ by reacting a chiral ligand with a desired metal ion (Cu I , Cu II , or V IV O). Generally, this method produces at least three species in solution: metal-free ligand, mononuclear, and dinuclear complexes. However, it is not easy to identify the active species that contribute to the overall reaction rate. Furthermore, the X-ray crystal structures of the above catalysts have never been determined, and this has restricted mechanistic investigations aimed at further improving the catalytic enantioselectivity and robustness. Given the success of Jacobsen's salen catalysts [6] in a broad range of asymmetric catalytic reactions, we decided to investigate whether coupled salen complexes would catalyze reactions that require two catalytic centers. Herein we describe the syntheses and crystal structures of a family of dicopper catalysts for the asymmetric oxidative coupling of 2-naphthol.The reaction of (1R,2R)-1,2-diaminocyclohexane (R,R-DACH) with 2,6-diformylphenol or its derivatives in the presence of Cu II gave yellow-green solids of 1 a-c (Scheme 1), Scheme 1. Structures of Schiff base dicopper(ii) complexes 1 a-c, macrocyclic ligands 2 a-c, and polyamino dicopper(ii) complexes 3 a-c.

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“…After continuous efforts to improve stoichiometric reactions, yielding in some cases high enantiomeric excesses because the coupling step was followed by selective precipitation of the chiral copper(II) amine-binaphthol complex with simultaneous racemization of the binaphthol [143,144,145,146], the first catalytic oxidative coupling was described by…”

Section: Copper-based Reactionsmentioning

confidence: 99%

Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals

Loxq

Manoury

Poli

et al. 2016

Coordination Chemistry Reviews

290

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Please cite this article as: P. Loxq, E. Manoury, R. Poli, E. Deydier, A. Labande, Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals, Coordination Chemistry Reviews (2015), http://dx. AbstractAxially chiral biaryl structures are unique systems encountered in various synthetic compounds such as BINAP and BINOL, polymers, but also in natural products presenting a pharmaceutical interest such as Vancomycin, Steganacin or Korupensamine. The axial chirality of these products, so-called atropisomerism, is induced by the restricted rotation around the aryl-aryl bond. This review will summarize the different strategies imagined by chemists to control such chirality, focusing on asymmetric catalytic processes with transition metals. Only transition metal complexes bearing chiral ligands will be considered and the core of this review will consist of the enantioselective coupling of two achiral substrates. Highlights 1. A review on the synthesis of axially chiral biaryls by asymmetric catalysis 2. Exhaustive description of chiral ligands used in the palladium-catalyzed SuzukiMiyaura cross-coupling reaction 3. Emerging reactions such as asymmetric direct C-H functionalization are presented 4. Asymmetric [2+2+2] cycloadditions catalyzed by group 9 transition metals are included

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A highly stereoselective synthesis of s(-)-[1,1′-binaphthalene]-2,2′-diol

Cited by 108 publications

References 11 publications

Structural analysis of sterically hindered 1,4‐diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study

Structural analysis of sterically hindered 1,4‐diols from the naturally occurring lignan hydroxymatairesinol a quantum chemical study

Structurally Defined Catalysts for Enantioselective Oxidative Coupling Reactions

Synthesis of axially chiral biaryl compounds by asymmetric catalytic reactions with transition metals

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