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Andrew Whiting's Outputs (122)

The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors (2017)
Journal Article
Haffez, H., Chisholm, D., Valentine, R., Pohl, E., Redfern, C., & Whiting, A. (2017). The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors. MedChemComm, 8(3), 578-592. https://doi.org/10.1039/c6md00680a

All-trans-retinoic acid (ATRA) and its synthetic analogues EC23 and EC19 direct cellular differentiation by interacting as ligands for the retinoic acid receptor (RARα, β and γ) family of nuclear receptor proteins. To date, a number of crystal struct... Read More about The molecular basis of the interactions between synthetic retinoic acid analogues and the retinoic acid receptors.

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines (2016)
Journal Article
Chisholm, D., Zhou, G., Pohl, E., Valentine, R., & Whiting, A. (2016). Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines. Beilstein Journal of Organic Chemistry, 12, 1851-1862. https://doi.org/10.3762/bjoc.12.174

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisa... Read More about Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines.

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring (2016)
Journal Article
Chisholm, D. R., Valentine, R., Pohl, E., & Whiting, A. (2016). Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring. Journal of Organic Chemistry, 81(17), 7557-7565. https://doi.org/10.1021/acs.joc.6b01110

A convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversio... Read More about Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring.

Alternative tandem cyclisation pathways in the reaction between imines and enones, (2016)
Journal Article
Girling, P., Batsanov, A., Calow, A., Shen, H., & Whiting, A. (2016). Alternative tandem cyclisation pathways in the reaction between imines and enones,. Tetrahedron, 72(8), 1105-1113. https://doi.org/10.1016/j.tet.2016.01.006

Dihydroisoquinoline reacts with Danishefsky's diene under Lewis acidic conditions or neat, to give low to moderate yields of the formal aza-Diels-Alder, [4+2]-cycloadduct. However, using methoxyvinyl methylketone with Lewis acid catalysis does not gi... Read More about Alternative tandem cyclisation pathways in the reaction between imines and enones,.

An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions (2015)
Journal Article
Chaiyaveij, D., Batsanov, A., Fox, M., Marder, T., & Whiting, A. (2015). An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions. Journal of Organic Chemistry, 80(19), 9518-9534. https://doi.org/10.1021/acs.joc.5b01470

Catalytic aerobic oxidation of phenyl hydroxycarbamate 1 and 1-hydroxy-3-phenylurea 2 using CuCl2 and 2-ethyl-2-oxazoline in methanol gave acyl nitroso species in situ, which were trapped in nitroso-Diels–Alder (NDA) reactions with various dienes to... Read More about An experimental and computational approach to understanding the reactions of acyl nitroso compounds in [4+2]-cycloadditions.

Heck-Mizoroki Coupling of Vinyliodide and Applications in The Synthesis of Dienes and Trienes (2015)
Journal Article
Whiting, A., Madden, K. S., David, S., & Knowles, J. P. (2015). Heck-Mizoroki Coupling of Vinyliodide and Applications in The Synthesis of Dienes and Trienes. Chemical Communications, 51(57), 11409-11412. https://doi.org/10.1039/c5cc03273c

Vinyliodide reacts chemoselectively under Heck-Mizoroki conditions with terminal alkenes, including vinylboronate esters, to give dienes. The resulting dienylboronates undergo Suzuki-Miyaura coupling with aryl, heteroaryl and alkenyl halides to acces... Read More about Heck-Mizoroki Coupling of Vinyliodide and Applications in The Synthesis of Dienes and Trienes.

A visible light induced α-H chlorination of alkylarenes with inorganic chloride under nanoAg@AgCl (2015)
Journal Article
Liu, S., Zhang, Q., Li, H., Yang, Y., Tiana, X., & Whiting, A. (2015). A visible light induced α-H chlorination of alkylarenes with inorganic chloride under nanoAg@AgCl. Chemistry - A European Journal, 21(27), 9671-9675. https://doi.org/10.1002/chem.201501439

An efficient, photocatalytic chlorination of alkylarene α-H groups using NaCl/HCl as chlorine source has been developed involving a radical mechanism under visible light (including sunlight) conditions. A chlorine radical is proposed to be formed by... Read More about A visible light induced α-H chlorination of alkylarenes with inorganic chloride under nanoAg@AgCl.

Regioisomeric and substituent effects upon the outcome of the reaction of 1-borodienes with nitrosoarene compounds (2015)
Journal Article
Eberlin, L., Carboni, B., & Whiting, A. (2015). Regioisomeric and substituent effects upon the outcome of the reaction of 1-borodienes with nitrosoarene compounds. Journal of Organic Chemistry, 80(13), 6574-6583. https://doi.org/10.1021/acs.joc.5b00593

A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp2 boron substituent, a one-pot hetero-Diels–Alder/ring con... Read More about Regioisomeric and substituent effects upon the outcome of the reaction of 1-borodienes with nitrosoarene compounds.

One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives (2015)
Journal Article
Pujol, A., Calow, A., Batsanov, A., & Whiting, A. (2015). One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives. Organic and Biomolecular Chemistry, 13(18), 5122-5130. https://doi.org/10.1039/c4ob02657h

The β-borylation reaction of α,β-unsaturated aldehyde-derived imines, formed in situ, has been studied using a one-pot methodology, as a route to β-boryl aldehydes. The instability of the β-boryl aldehydes meant that a derivatisation process was requ... Read More about One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives.

Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: an analytical and theoretical investigation (2014)
Journal Article
Calow, A., Carbó, J., Cid, J., Fernández, E., & Whiting, A. (2014). Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: an analytical and theoretical investigation. Journal of Organic Chemistry, 79(11), 5163-5172. https://doi.org/10.1021/jo5007366

A combination of in situ IR spectroscopy (ReactIR) and DFT calculations have been used to understand what factors govern the selectivity in the addition of primary amines to α,β-unsaturated aldehydes and ketones, i.e., 1,2- versus 1,4-addition. It ha... Read More about Understanding α,β-unsaturated imine formation from amine additions to α,β-unsaturated aldehydes and ketones: an analytical and theoretical investigation.

Asymmetric synthesis and application of homologous pyrroline-2-alkylboronic acids: Identification of the B-N distance for eliciting bifunctional catalysis of an asymmetric aldol reaction (2014)
Journal Article
Batsanov, A., Georgiou, I., Girling, P., Pommier, L., Shen, H., & Whiting, A. (2014). Asymmetric synthesis and application of homologous pyrroline-2-alkylboronic acids: Identification of the B-N distance for eliciting bifunctional catalysis of an asymmetric aldol reaction. Asian Journal of Organic Chemistry, 3(4), 470-479. https://doi.org/10.1002/ajoc.201300127

Homoboroproline has been shown to be an efficient bifunctional catalyst for the aldol reaction of acetone with p-nitrobenzaldehyde by using in situ Lewis acid tuning of the boronic acid esterification with a diol. Herein, asymmetric syntheses of homo... Read More about Asymmetric synthesis and application of homologous pyrroline-2-alkylboronic acids: Identification of the B-N distance for eliciting bifunctional catalysis of an asymmetric aldol reaction.

Application of Synthetic Photostable Retinoids Induces Novel Limb and Facial Phenotypes During Chick Embryogenesis In Vivo (2014)
Journal Article
Lopez-Real, R., Budge, J., Marder, T., Whiting, A., Hunt, P., & Przyborski, S. (2014). Application of Synthetic Photostable Retinoids Induces Novel Limb and Facial Phenotypes During Chick Embryogenesis In Vivo. Journal of Anatomy, 224(4), 392-411. https://doi.org/10.1111/joa.12147

We have recently developed a range of synthetic retinoid analogues which include the compounds EC23 and EC19. They are stable on exposure to light and are predicted to be resistant to the normal metabolic processes involved in the inactivation of ret... Read More about Application of Synthetic Photostable Retinoids Induces Novel Limb and Facial Phenotypes During Chick Embryogenesis In Vivo.

Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz (2014)
Journal Article
La Cascia, E., Sanz, X., Bo, C., Whiting, A., & Fernandez, E. (2014). Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz. Organic and Biomolecular Chemistry, 13(5), 1328-1332. https://doi.org/10.1039/c4ob02478h

The adduct [MeO → Bpin–Bpin]− efficiently mediates the β-boration of α,β-unsaturated imines formed in situ. The use of chiral phosphines as additives, and in particular the chiral phosphine (S)-MeBoPhoz, enables the catalytic asymmetric reaction to p... Read More about Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz.

Design and biological evaluation of synthetic retinoids: Probing length vs. stability vs. activity (2013)
Journal Article
Clemens, G., Flower, K., Gardner, P., Henderson, A., Knowles, J., Marder, T., …Przyborski, S. (2013). Design and biological evaluation of synthetic retinoids: Probing length vs. stability vs. activity. Molecular bioSystems, 9(12), 3124-3134. https://doi.org/10.1039/c3mb70273a

All trans-retinoic acid (ATRA) is widely used to direct the differentiation of cultured stem cells. When exposed to the pluripotent human embryonal carcinoma (EC) stem cell line, TERA2.cl.SP12, ATRA induces ectoderm differentiation and the formation... Read More about Design and biological evaluation of synthetic retinoids: Probing length vs. stability vs. activity.

Facile synthesis of a 1,1’-desymmetrised ferrocene backbone and its one-pot double-“click” functionalisation (2013)
Journal Article
Ilyashenko, G., Al-Safadi, R., Donnan, R., Dubrovka, R., Pancholi, J., Watkinson, M., & Whiting, A. (2013). Facile synthesis of a 1,1’-desymmetrised ferrocene backbone and its one-pot double-“click” functionalisation. RSC Advances, 3(38), 17081-17087. https://doi.org/10.1039/c3ra43054e

A one-pot, four-component, copper-catalysed double-“click” functionalisation of a novel 1,1′-desymmetrised ferrocene backbone is reported. Using an array of alkynes and azides, a library of ferrocene compounds was developed, demonstrating the scope o... Read More about Facile synthesis of a 1,1’-desymmetrised ferrocene backbone and its one-pot double-“click” functionalisation.

A selective transformation of enals into chiral γ-amino alcohols (2013)
Journal Article
Calow, A., Batsanov, A., Pujol, A., Solé, C., Fernández, E., & Whiting, A. (2013). A selective transformation of enals into chiral γ-amino alcohols. Organic Letters, 15(18), 4810-4813. https://doi.org/10.1021/ol4022029

A one-pot synthesis of chiral amino alcohols from α,β-unsaturated aldehydes is reported which circumvents competitive 1,2- versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselect... Read More about A selective transformation of enals into chiral γ-amino alcohols.

Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis (2013)
Journal Article
Liu, S., Yang, Y., Liu, X., Ferdousi, F., Batsanov, A., & Whiting, A. (2013). Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis. European Journal of Organic Chemistry, 2013(25), 5692-5700. https://doi.org/10.1002/ejoc.201300560

The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65–68 °C generally avoiding racemization. 3,4,5... Read More about Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis.

Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction (2013)
Journal Article
Calow, A., Solé, C., Whiting., A., & Fernández, E. (2013). Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction. ChemCatChem, 5(8), 2233-2239. https://doi.org/10.1002/cctc.201300113

The stereoselective synthesis of γ-aminoalcohols from the catalytic asymmetric β-boration of α,β-unsaturated imine precursors has been streamlined with the use of Cu2O as the catalyst, readily accessible (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binap... Read More about Base-free β-boration of α,β-unsaturated imines catalysed by Cu2O with concurrent enhancement of asymmetric induction.

A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds (2013)
Journal Article
Tripoteau, F., Eberlin, L., Fox, M., Carboni, B., & Whiting, A. (2013). A novel, efficient synthesis of N-aryl pyrroles via reaction of 1-boronodienes with arylnitroso compounds. Chemical Communications, 49(47), 5414-5416. https://doi.org/10.1039/c3cc42227e

A one-pot hetero-Diels–Alder/ring contraction cascade is presented from the reaction of 1-boronodienes and arylnitroso derivatives to derive N-arylpyrroles in moderate to good yields (up to 82%).