A facile synthesis of 3 or 3,3′-substituted binaphthols and their applications in the asymmetric addition of diethylzinc to aldehydes

Guo, Qing; Lu, Yongna; Liu, Bing; Li, Jin‐Shan

doi:10.1016/j.jorganchem.2005.12.042

Cited by 21 publications

(5 citation statements)

References 24 publications

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“…After ( S )-BINOL-MOM was treated with 3 equiv of n BuLi in THF at −78 °C to room temperature, it was reacted with quinoline at 0 °C to room temperature to give 273 (Scheme ). Addition of nitrobenzene and water followed by heating at reflux converted 273 to ( S )- 274 in 86% yield in this one-pot reaction. When 1.2 equiv of n BuLi was used for the ortho-lithiation, the monosubstituted product ( S )- 275 was obtained in 55% yield.…”

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

“…When ( S )-BINOL-MOM was ortho-lithiated with 1.2 equiv and 1.9 equiv of n BuLi followed by reaction with chloromethyl methyl ether, the 3-mono- and 3,3′-di(methoxymethyl)-substituted products ( S )- 221 and ( S )- 222 were obtained in 57% and 80% yields, respectively (Scheme ). After removal of the protecting groups with 6 N HCl in MeOH/CH 2 Cl 2 , the resulting compounds ( S )- 223 and ( S )- 224 in combination with Ti(O i Pr) 4 were used to catalyze the asymmetric reaction of ZnEt 2 with aryl aldehydes.…”

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

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Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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“…A search for 2-hydroxyphenylquinoline in the Cambridge Structural Database (CSD; Version 2021.3.0, last update November 2021; Groom et al, 2016) gave 29 hits, which exhibit structural diversity with interesting properties, such as chemical (Alexandre et al, 2020;Han et al, 2017;Yao et al, 2012;Guo et al, 2006), physical (Zheng et al, 2013;Elbert et al, 2017) and biological (Mulakayala et al, 2012).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-(2-hydroxyphenyl)quinoline-6-sulfonamide

Benarous¹,

Slimane²,

Bougueria³

et al. 2022

Acta Cryst E

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In the title compound, C15H12N2O3S, there are two molecules (A and B) in the asymmetric unit. The attached phenol and quinoline moieties of each molecule are almost coplanar with a dihedral angle of 6.05 (15)° for molecule A and 1.89 (13)° for molecule B. The crystal structure features N—H...O and C—H...O hydrogen bonds, C—H...π interactions and π–π stacking interactions. Hirshfeld surface analysis indicates that the most significant contacts in the crystal packing are C...H/H...C (29.2%), O...H/H...O (28.6%) and H...H (28.5%).

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“…1,1 0 -Binaphthol and its derivatives are used as chiral auxiliaries in stereoselective organic synthesis (Nishizawa et al, 1981;Noyori et al, 1979;Naruse et al,1988;Hesemann & Moreau, 2003;Teo et al, 2005;Guo et al, 2006). These compounds can be prepared by various methods (Feringa & Wynberg, 1977;Toda et al, 1989;Nakajima et al, 1999;Xin et al, 2002).…”

Section: Commentmentioning

confidence: 99%

Methyl 2,2′,7′-trihydroxy-1,1′-binaphthalene-3-carboxylate acetone solvate

Wang

Lian

2006

Acta Cryst E

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In the title compound, C22H16O5, the two naphthyl units are approximately perpendicular. The 3‐naphthylcarboxyl group and the ortho‐hydroxyl group are involved in an intermolecular O—H⋯O hydrogen bond with O⋯O = 2.606 (2) Å. Molecules related by a glide plane are linked by an intermolecular O—H⋯O hydrogen bond with O⋯O = 2.747 (2) Å, creating a spiral. A solvent molecule is an acceptor in an O—H⋯O hydrogen bond with O⋯O = 2.700 (2) Å.

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A facile synthesis of 3 or 3,3′-substituted binaphthols and their applications in the asymmetric addition of diethylzinc to aldehydes

Cited by 21 publications

References 24 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

Crystal structure and Hirshfeld surface analysis of 2-(2-hydroxyphenyl)quinoline-6-sulfonamide

Methyl 2,2′,7′-trihydroxy-1,1′-binaphthalene-3-carboxylate acetone solvate

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