Quinoid BINOL-type compounds as a novel class of chiral ligands

Minatti, Ana; Dötz, Karl Heinz

doi:10.1016/j.tetasy.2005.08.026

Cited by 38 publications

(13 citation statements)

References 47 publications

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“…This compound was synthesized in 97.5% yield (mp 208-209°C) from optically pure (R)-(+)-2,2′-dihydroxy-1,1′-binaphthyl following a reported procedure [39]. Characterizations by 1 H NMR are consistent with reported data.…”

Section: Synthesis Of (R)-(+)-66′-dibromo-22′-dihydroxy-11′-binaphsupporting

confidence: 65%

Synthesis of a series of soluble main-chain chiral nonracemic poly(alkyl-aryl ketone)

Wei¹,

Wang²,

Wu³

et al. 2008

Express Polym. Lett.

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Abstract.A series of main-chain chiral polyketones have been synthesized through condensation polymerization of a dihalide and a diketone with optically pure binaphthyl moiety as linkage in the polymer backbone. The solubility of the polymers can be easily enhanced by substituents at the alpha position next to the carbonyl groups. Reducing the steric hindrance of the substituents in the monomers increases the reactivity of the polymerization. The chiral polymers exhibit large optical rotations. Circular Dichroism (CD) spectra of the polymers are similar to those of the corresponding monomers. The novel synthetic strategy may have great impact on future development of palladium catalyzed condensation polymerizations. The highly soluble chiral polymers synthesized allow for preparation of materials in the form of thin films and have potentials applications in various areas such as chiral separation and recognition.

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Section: Synthesis Of (R)-(+)-66′-dibromo-22′-dihydroxy-11′-binaphsupporting

confidence: 65%

Synthesis of a series of soluble main-chain chiral nonracemic poly(alkyl-aryl ketone)

Wei¹,

Wang²,

Wu³

et al. 2008

Express Polym. Lett.

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“…The etherification of hydroxyl groups of S‐2 could be carried out through a reaction with n ‐octyl bromide in the presence of K 2 CO 3 in a refluxing CH 3 CN solution 24–26 . S‐M‐2 was synthesized according to the literature,27, 28 and S‐M‐3 was synthesized according to the literature 29, 30 . S‐M‐1 , S‐M‐2 , and S‐M‐3 could serve as the monomers for the synthesis of the desired chiral polymers.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and enantioselectivities of soluble polymers incorporating optically active binaphthyl and binaphthol

Zou

Zhang

Cheng

et al. 2007

J of Applied Polymer Sci

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A polymer (P-1) was synthesized through the polymerization of (S)-6,60 -dibromo-3,3 0 -dibutyl-1,1 0 -binaphthol with (S)-2,2 0 -dioctoxy-1,1 0 -binaphthyl-6,6 0 -boronic acid in a Pd-catalyzed Suzuki reaction, and another polymer (P-2) was synthesized through the polymerization of (S)-6,60 -dioctoxy-1,1 0 -binaphthyl in a Pd-catalyzed Sonogashira reaction. The two polymers showed good solubility in some common solvents and were characterized with NMR, Fourier transform infrared, gel permeation chromatography, and circular dichroism spectroscopy. The application of the chiral monomers and polymers in the asymmetric addition of diethyl zinc to benzaldehyde was studied. The results indicated that P-1, P-2, and the monomer (S)-3,3 0 -dibutyl-1,1 0 -binaphthol were efficient ligands in the asymmetric addition of diethyl zinc to benzaldehyde. The chiral polymer ligands P-1 and P-2 were more efficient than their monomeric version, (S)-3,3 0 -dibutyl-1,1 0 -binaphthol, and could be easily recovered and reused without a loss of catalytic activity or enantioselectivity.

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“…26 The phosphate group was introduced by reacting with POCl 3 , hydrolyzing with water and washing with 2 M HCl, which afforded pure PA 3 and PA 4 after recrystallization. 29 The main synthetic steps for PA 1 and PA 2 have been reported in literature 30,31 (Scheme 1).…”

Section: Synthesis Of 22imentioning

confidence: 99%

Design and synthesis of new alkyl‐based chiral phosphoric acid catalysts

Tang

Fang

et al. 2019

Chirality

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Using chiral BINOL‐derived phosphoric acids (PA's) to activate substrates for enhanced reactivity is now regarded as a powerful strategy to control enantioselectivity in asymmetric synthesis. Generally, most substituents at the 3,3′‐positions of BINOL PA's are aryl derivatives. These derivatives are pivotal in attaining high selectivity. PA's with alkyl substituents in these positions have rarely been reported. Herein, we introduced alkyl‐based substituents at the 3,3′‐position of PA's. These new potential catalysts, if applied in reactions, may allow altered noncovalent interactions (as opposed to the typical aryl substituents in these positions) with substrates used in chiral PA‐catalyzed chemistry in the future.

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Quinoid BINOL-type compounds as a novel class of chiral ligands

Cited by 38 publications

References 47 publications

Synthesis of a series of soluble main-chain chiral nonracemic poly(alkyl-aryl ketone)

Synthesis of a series of soluble main-chain chiral nonracemic poly(alkyl-aryl ketone)

Synthesis and enantioselectivities of soluble polymers incorporating optically active binaphthyl and binaphthol

Design and synthesis of new alkyl‐based chiral phosphoric acid catalysts

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