Absolute stereochemical determination of 1,2‐diols via complexation with dinaphthyl borinic acid

Kohlbouni, Saeedeh Torabi; Sarkar, Aritra; Zhang, Jun; Li, Xiaoyong; Borhan, Babak

doi:10.1002/chir.23223

Cited by 6 publications

(5 citation statements)

References 21 publications

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“…VT 1 H NMR experiments revealed that sharp signals of non‐equivalent naphthyl groups are observed below 248 K (Figure S46, Supporting Information). A similar behaviour was previously reported for related derivatives [18–20] . The desired boronic acid 1 was obtained as a sole product in high yield when the transmetallation was performed by rapid quenching of intermediate 8‐bromo‐1‐lithionaphthalene with excess of B(OMe) 3 at very low temperature (below −100 °C).…”

Section: Resultssupporting

confidence: 81%

“…A similar behaviour was previously reported for related derivatives. [18][19][20] The desired boronic acid 1 was obtained as a sole product in high yield when the transmetallation was performed by rapid quenching of intermediate 8-bromo-1-lithionaphthalene with excess of B(OMe) 3 at very low temperature (below À 100 °C). This modification apparently prevented decomposition of intermediate ate complex generating (8-bromonaphthalene-1-yl)dimethoxyborane 1 a which forms 1 b after subsequent attack with unreacted aryllithium.…”

Section: Synthesismentioning

confidence: 99%

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Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes

Luliński

Durka

Marek

et al. 2022

Chemistry A European J

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The approach to a series of six‐ and seven‐membered oxaboraheterocycles based on naphthalene or biphenyl backbones was developed. The key synthetic step involved Br/Li exchange in respective potassium (bromoaryl)trifluoroborates followed by quenching with selected electrophiles (CO2, DMF, Me2Si(H)Cl) and hydrolytic workup. Two ring‐expanded benzoxaborole congeners were obtained by an additional reduction step with LiAlH4 or NaBH4. The obtained boracyclic compounds were characterized in detail by NMR spectroscopy and single‐crystal X‐ray diffraction. Specifically, biphenyl‐based systems show dynamic behaviour interpreted in terms of inversion of non‐planar seven‐membered boraheterocycles. The acidity of the obtained compounds varies very strongly (pKa ranges from 3.1–9.6) depending on their structure. Due to the enhanced boron Lewis acidity, selected compounds were used as a basis for luminescent complexes with 8‐hydroxyquinoline. A strong phase‐dependent variation of emission‐band maximum (480–527 nm) and photoluminescence quantum yield (10–95 %) was observed, which was rationalized in terms of specific aggregation effects.

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Section: Resultssupporting

confidence: 81%

Section: Synthesismentioning

confidence: 99%

Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes

Luliński

Durka

Marek

et al. 2022

Chemistry A European J

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“…It is one of the chiroptical techniques which can be used to elucidate structural information complementary to NMR and X-ray. 1 It is especially powerful to determine the absolute configurations and conformations [2][3][4][5] and to probe the molecular orientations in a complex. 6,7 In recent years, ICD has drawn a lot of attention due to its potential applications, such as in the field of new materials, 8 heterogeneous catalysis, 9 drug delivery, 10 chiral nanoarchitectures, 11 and electroptical devices.…”

Section: Introductionmentioning

confidence: 99%

Tunable induced circular dichroism in gels

et al. 2022

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The ICD phenomenon has drawn a lot of attention in recent years in applicable fields such as chiral sensing and chiroptical devices. In this work, we first gaze at the issues of thin spin‐coated films not being able to deliver consistent ICD signals. A hypothesis of the underlying problem is proposed through a brief elucidation of the spin‐coating process. To confirm and eliminate the uncontrollable dynamic factors with spin coating, we then dedicate our efforts to develop a new gel system based on chiral L‐/D‐N′,N′‐Dibenzoyl‐cystine. Achiral dye molecules are intercalated in a DBC gel through a “one‐step” preparation procedure. Compared to the former spin‐coating system, significantly improved reproducibility of the new gel system is demonstrated. Besides, the ICD signals can be customized in a broad spectral range (wavelength tunability) by substituting dye molecules. Finally, we discuss the potential applications of this interesting system.

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“…Molecules 2-18 contain no aromatic groups and thus show no CD signals at the wavelength above 200 nm;while molecules 19-31 contain one phenyl group and show weak/negligible CD signals at the common concentrations ( Figures S1-S5). Chiroptical sensing of some of these molecules (2-4, [22] 8-11, 22,a nd 23 [7,23] 15-17 and 26-28, [24] 30, [25] 31 [4] )h ave been achieved with other sensor assays,but others (5-7, 12-14, 18, 21, 24, 25, 29)a re not reported presumably because it is too challenging for the known sensors.For example,bisporphyrin tweezer [26] is able to give induced CD in the presence of many epoxy alcohols but shows no CD signals when adding epoxy alcohol 5-an important intermediate in organic synthesis.…”

Section: Resultsmentioning

confidence: 99%

A Green and Wide‐Scope Approach for Chiroptical Sensing of Organic Molecules through Biomimetic Recognition in Water

et al. 2020

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Optical chirality sensing has attracted a lot of interest due to its potential in high‐throughput screening in chirality analysis. A molecular sensor is required to convert the chirality of analytes into optical signals. Although many molecular sensors have been reported, sensors with wide substrate scope remain to be developed. Herein, we report that the amide naphthotube‐based chirality sensors have an unprecedented wide scope for chiroptical sensing of organic molecules. The substrates include, but are not limited to common organic products in asymmetric catalysis, chiral molecules with inert groups or remote functional groups from their chiral centers, natural products and their derivatives, and chiral drugs. The effective chirality sensing is based on biomimetic recognition in water and on effective chirality transfer through guest‐induced formation of a chiral conformation of the sensors. Furthermore, the sensors can be used in real‐time monitoring on reaction kinetics in water and in determining absolute configurations and ee values of the products in asymmetric catalysis.

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Absolute stereochemical determination of 1,2‐diols via complexation with dinaphthyl borinic acid

Abstract: This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record. Please cite this article as

Cited by 6 publications

References 21 publications

Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes

Expedient Synthesis of Oxaboracyclic Compounds Based on Naphthalene and Biphenyl Backbone and Phase‐Dependent Luminescence of their Chelate Complexes

Tunable induced circular dichroism in gels

A Green and Wide‐Scope Approach for Chiroptical Sensing of Organic Molecules through Biomimetic Recognition in Water

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