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(2021)
Catalytic Applications of TiO2. In Titanium Dioxide (TiO2) and Its Applications
L. Albarella, D. Musumeci, D. Sica (2001)
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V. Piccialli (2000)
RuO4‐Catalyzed Oxidative Cyclization of 1,6‐Dienes to trans‐2,6‐Bis(hydroxymethyl)tetrahydropyranyldiols. A Novel Stereoselective Process.ChemInform, 31
V. Piccialli, N. Borbone, G. Oliviero (2007)
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T. Donohoe, S. Butterworth (2003)
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S. Roth, Sabrina Goehler, Huan Cheng, C. Stark (2005)
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V. Piccialli, N. Cavallo (2001)
Improved RuO4-catalysed oxidative cyclisation of geraniol-type 1,5-dienes to cis-2,5-bis(hydroxymethyl)tetrahydrofuranyldiolsTetrahedron Letters, 42
Sabrina Zaccaria, N. Borbone, G. Oliviero, S. D’Errico, V. Piccialli (2017)
Pyridinium chlorochromate chemistry. New insight into oxidation of tetrahydrofuransArkivoc, 2017
V. Piccialli (2007)
Oxidative cyclization of dienes and polyenes mediated by transition-metal-oxo speciesSynthesis, 2007
Cory Beshara, A. Hall, R. Jenkins, K. Jones, T. Jones, N. Killeen, Paul Taylor, Stephen Thomas, N. Tomkinson (2005)
A General Method for the a-Acyloxylation of Carbonyl CompoundsOrganic Letters
V. Piccialli, G. Oliviero, N. Borbone, A. Tuzi, R. Centore, A. Hemminki, Matteo Ugolini, V. Cerullo (2009)
Discovery of a new PCC-mediated stereoselective oxidative spiroketalization process. An access to a new type of poly-THF spiroketal compound displaying anticancer activityOrganic and Biomolecular Chemistry, 7
K. Vinod, Puttaswamy, K. Gowda (2010)
Os(VIII) as an efficient homogeneous catalyst for the oxidative decolorization of methylene blue dye with alkaline chloramine-T: Kinetic, mechanistic, and platinum metal ions reactivity studiesIndustrial & Engineering Chemistry Research, 49
M. Uyanik, D. Suzuki, T. Yasui, K. Ishihara (2011)
In situ generated (hypo)iodite catalysts for the direct α-oxyacylation of carbonyl compounds with carboxylic acids.Angewandte Chemie, 50 23
V. Piccialli, Sabrina Zaccaria, G. Oliviero, S. D’Errico, V. D’Atri, N. Borbone (2012)
Insight into Pyridinium Chlorochromate Chemistry: Catalytic Oxidation of Tetrahydrofuran Compounds and Synthesis of UmbelactoneEuropean Journal of Organic Chemistry, 2012
Xin Chen, Yangchun Xin, Zhichao Zhao, Yuqing Hou, Xiang-xiang Wang, Wen-Jin Xia, Ya-Min Li (2021)
Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones.The Journal of organic chemistry
V. Piccialli, S. D’Errico, N. Borbone, G. Oliviero, R. Centore, Sabrina Zaccaria (2013)
A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP DiolsEuropean Journal of Organic Chemistry, 2013
(2014)
Catalytic Applications of TiO 2
P. Prasad, Rambabu Reddi, Sudalai Arumugam (2018)
Recent methods for the synthesis of α-acyloxy ketones.Organic & biomolecular chemistry, 16 48
S. Roth, C. Stark (2006)
Efficient oxidative cyclization of 1,6-dienes: a highly diastereoselective entry to substituted tetrahydropyrans.Angewandte Chemie, 45 37
V. Piccialli, Sabrina Zaccaria, N. Borbone, G. Oliviero, S. D’Errico, A. Hemminki, V. Cerullo, Valentina Romano, A. Tuzi, R. Centore (2010)
Discovery of a novel one-step RuO4-catalysed tandem oxidative polycyclization/double spiroketalization process. Access to a new type of polyether bis-spiroketal compound displaying antitumour activityTetrahedron, 66
V. Piccialli (2014)
Ruthenium Tetroxide and Perruthenate Chemistry. Recent Advances and Related Transformations Mediated by Other Transition Metal Oxo-speciesMolecules, 19
J. Lee, Yong Jin, Ju-Hee Choi (2001)
Synthesis of α-acetoxy and formyloxy ketones by thallium(III) promoted α-oxidationChemical Communications
T. Connolly, John Considine, Z. Ding, Brian Forsatz, Mellard Jennings, Michael Macewan, K. Mccoy, D. Place, Archana Sharma, K. Sutherland (2010)
Efficient Synthesis of 8-Oxa-3-aza-bicyclo[3.2.1]octane Hydrochloride†Organic Process Research & Development, 14
W. Mijs, C. Jonge (1986)
Organic Syntheses by Oxidation with Metal Compounds
A. Okumura, Mie Kitani, M. Murata (1994)
Kinetic Studies of the Catalytic Oxygen Exchange of Chromate Ions with Water by Periodate IonsBulletin of the Chemical Society of Japan, 67
M. Champdoré, M. Lasalvia, V. Piccialli (1998)
OsO4-Catalyzed oxidative cyclization of geranyl and neryl acetate to cis-2,5-bis(hydroxymethyl)tetrahydrofurans
molbank Short Note Short Note (±)-((2S,5R)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate ()-((2S,5R)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate Vincenzo Piccialli Vincenzo Piccialli Department of Chemical Sciences, University of Naples Federico II, via Cintia 4, 80126 Naples, Italy; vinpicci@unina.it Department of Chemical Sciences, University of Naples Federico II, Via Cintia 4, 80126 Naples, Italy; vinpicci@unina.it Abstract: In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised in three steps by the stereoselective RuO4-catalysed oxidative cyclisation of 1,5-hexadiene, followed Abstract: In this note we report the synthesis of a doubly acylated cis-THF-diol product synthesised by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new in three steps by the stereoselective RuO -catalysed oxidative cyclisation of 1,5-hexadiene, followed developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. by benzoylation and acetylation. This substance is one of the substrates chosen to probe a new This new derivative was fully characterised by spectroscopic methods. developed oxidative procedure to transform bis-acylated THF-diols into bis-acylated 1,4-diketones. This new derivative was fully characterised by spectroscopic methods. 1 13 Keywords: bis-acylated α-bis-hydroxymethyl-tetrahydrofuran; oxidative cyclization; H-NMR; C- NMR; FTIR; HRESIMS Keywords: bis-acylated -bis-hydroxymethyl-tetrahydrofuran; oxidative cyclization; H-NMR; C-NMR; FTIR; HRESIMS 1. Introduction 1. Introduction Oxidation methods, mediated or catalysed by transition metal oxo-species, are a class of processes of central importance in organic synthesis [1–4]. Some of them play an Oxidation methods, mediated or catalysed by transition metal oxo-species, are a important role in industrial processes [5,6]. As part of our ongoing studies on oxidative class of processes of central importance in organic synthesis [1–4]. Some of them play processes catalysed by transition metal oxo-species [7–10], we recently developed a new an important role in industrial processes [5,6]. As part of our ongoing studies on oxida- chlorochromatoperiodate (CCP)-catalysed process that allows the synthesis of bis-α- tive processes catalysed by transition metal oxo-species [7–10], we recently developed a acyloxy-1,4- and -1,5-diketones (2, Scheme 1) through the oxidative opening of bis- new chlorochromatoperiodate (CCP)-catalysed process that allows the synthesis of bis-- acylated 2,5-dihydroxyalkyl-substituted tetrahydrofurans and tetrtahydropyrans acyloxy-1,4- and -1,5-diketones (2, Scheme 1) through the oxidative opening of bis-acylated Citation: Piccialli, V. (±)-((2S,5R)-5- (acylated THF- and THP-diols, 1, Scheme 1), respectively [11]. CCP is a powerful reagent, 2,5-dihydroxyalkyl-substituted tetrahydrofurans and tetrtahydropyrans (acylated THF- Citation: Piccialli, V. ()-((2S,5R)-5- (Acetoxymethyl)tetrahydrofuran-2- and generated THP-diols, by the 1, condensation o Scheme 1), respfectively pyridinium [11]. chlo CCProchromate (PCC) and is a powerful reagent, periodic generated acid by (Acetoxymethyl)tetrahydrofuran-2- yl)methyl Benzoate. Molbank 2022, the [12], c conden apablsation e of oxi of dis pyridinium ing THF-con chlor taini ochr ng compoun omate (PCC) ds of and varyin periodic g struc acid tura[l12 co ],mplexit capable y yl)methyl Benzoate. Molbank 2022, 2022, x. https://doi.org/10.3390/xxxxx of [8,9 oxidising ]. Conside Tr HF-containing ing that THF- compounds and THP-diol ofs varying can be synthesised th structural complexity rough the ruthenium [8,9]. Consid- - 2022, M1349. https://doi.org/ ering [13–17 that ] and osmi THF- and um- THP-diols [18,19] catacan lysed oxi be synthesised dative cycliz thr atough ion of 1,5- the r a uthenium- nd 1,6-dien [13 es – (S 17 ch ] e and me 10.3390/M1349 Academic Editor: Nicola Della Ca osmium- 1), respectively, our process allows the [18,19] catalysed oxidative cyclization regioselec of tive 1,5- bis-ketoac and 1,6-dienes yloxylation of th (Scheme 1 e ),starting respec- Academic Received: 9 Editor: Februa Nicola ry 2022 Della Ca tively, our process allows the regioselective bis-ketoacyloxylation of the starting diene. diene. Accepted: 1 March 2022 Received: 9 February 2022 Published: 4 March 2022 Accepted: 1 March 2022 1.Oxidative 1 3 ( ) 3 OCOR O R n 3 R R CCP (PCC /H IO ) R cyclisation cat. 5 6 1 Publisher’s Note: MDPI stays 2 4 Published: 4 March 2022 4 ( ) R R R R ( ) R 1,2 2 1,2 neutral with regard to jurisdictional R 2. Acylation Oxidative cleavage 4 OCOR OCOR R O OCOR Publisher’s Note: MDPI stays neutral of the THF ring claims in published maps and 1 n=1,2 with regard to jurisdictional claims in institutional affiliations. published maps and institutional affil- Scheme Scheme 1 1.. CC CCP-catalysed P-catalysed synthesis synthesis o of f bi bis- s-α-acyloxy-1,4- -acyloxy-1,4- a and nd -1,5- -1,5-diketones. diketones. iations. The keen interest of synthetic organic chemists towards -acyloxy ketones is demon- The keen interest of synthetic organic chemists towards α-acyloxy ketones is strated by the numerous methods developed to obtain these substances (see for example demonstrated by the numerous methods developed to obtain these substances (see for Copyright: © 2022 by the authors. Refs. [20–24]). However, the synthesis and the chemistry of bis--acyloxy diketones such as example Refs. [20–24]). However, the synthesis and the chemistry of bis-α-acyloxy Submitted for possible open access Copyright: © 2022 by the author. 2 (Scheme 1) are largely unexplored. The possibility of differentiating the chemistry of the publication under the terms and diketones such as 2 (Scheme 1) are largely unexplored. The possibility of differentiating Licensee MDPI, Basel, Switzerland. two -acyloxy ketone functionalities, the timing of their synthetic exploitation, as well as conditions of the Creative Commons the chemistry of the two α-acyloxy ketone functionalities, the timing of their synthetic This article is an open access article the transformation of bis--acyloxy diketones into five- or six-membered dihydroxyalkyl- Attribution (CC BY) license exploitation, as well as the transformation of bis-α-acyloxy diketones into five- or six- distributed under the terms and substituted heterocycles, are all appealing synthetic goals. All of the above considerations (https://creativecommons.org/license membered dihydroxyalkyl-substituted heterocycles, are all appealing synthetic goals. All conditions of the Creative Commons s/by/4.0/). prompted us to further investigate this transformation, with the aim of also broadening its of the above considerations prompted us to further investigate this transformation, with Attribution (CC BY) license (https:// scope as well as of extending our synthetic procedure to acid or PCC-sensitive substrates. the aim of also broadening its scope as well as of extending our synthetic procedure to creativecommons.org/licenses/by/ To this end, we planned the synthesis of a set of bis-acylated/bis-protected THF-diols acid or PCC-sensitive substrates. To this end, we planned the synthesis of a set of bis- 4.0/). Molbank 2022, 2022, x. https://doi.org/10.3390/xxxxx www.mdpi.com/journal/molbank Molbank 2022, 2022, M1349. https://doi.org/10.3390/M1349 https://www.mdpi.com/journal/molbank Molbank 2022, 2022, x FOR PEER REVIEW 2 of 4 Molbank 2022, 2022, M1349 2 of 4 acylated/bis-protected THF-diols possessing diverse acyl- or hydroxyl-protecting groups, possessing diverse acyl- or hydroxyl-protecting groups, able to be selectively removed. We able to be selectively removed. We report here the synthesis of one of these substances, report here the synthesis of one of these substances, namely the title compound, that was namely the title compound, that was synthesised by the RuO4-catalysed stereoselective synthesised by the RuO -catalysed stereoselective oxidative cyclisation of commercially oxidative cyclisation of commercially available 1,5-hexadiene, followed by the available 1,5-hexadiene, followed by the transformation of the alcohol functions into acetate transformation of the alcohol functions into acetate and benzoate groups. and benzoate groups. 2. Results and Discussion 2. Results and Discussion The oxidative cyclization of 1,5-hexadiene (3, Scheme 2) was performed according to The oxidative cyclization of 1,5-hexadiene (3, Scheme 2) was performed according to aa h highly ighly e eff ficient ficient RuO RuO 4-catalysed -catalysed oxid oxidative ative cyc cyclisation lisation procedur proceduree pr previous eviously ly d developed eveloped by by Stark an Stark and d co-workers co-workers [[15]. The obtained THF-diol produc 15]. The obtained THF-diol productt 4 4 w was as mono-ben mono-benzoylated zoylated with BzCl in pyridine and then acetylated with Ac O/pyridine, to give the title compound with BzCl in pyridine and then acetylated with Ac2O/pyridine, to give the title compound 5 5 wh which ich wa was s obta obtained ined in in ppur ure form e form by by prepar preparative ative TLTLC C (34% (34% for thr for ee steps). Spe three steps). cSpectral tral data 1 13 1 13 data ( H-and C-NMR, FT-IR, HRESIMS) for 5 (see Supplementary Materials) were in full ( H-and C-NMR, FT-IR, HRESIMS) for 5 (see Supplementary Materials) were in full agreement with the reported structure. agreement with the reported structure. Scheme 2. Synthesis of ()-((2S,5R)-5-(acetoxymethyl)tetrahydrofuran-2-yl)methyl benzoate (5). Scheme 2. Synthesis of (±)-((2S,5R)-5-(acetoxymethyl)tetrahydrofuran-2-yl)methyl benzoate (5). 3. Materials and Methods 3. Materials and Methods 3.1. General Information 3.1. General Information All reagents were purchased in the highest commercial quality (Aldrich, Milano, All reagents were purchased in the highest commercial quality (Aldrich) and used Italy) and used without further purification. Reactions were monitored by thin-layer without further purification. Reactions were monitored by thin-layer chromatography chromatography carried out on precoated silica gel plates (Merck 60, F , 0.25 mm thick). carried out on precoated silica gel plates (Merck 60, F254, 0.25 mm thick). Na2SO4 was used Na SO was used as a drying agent for aqueous work-up. H-NMR experiments were 2 4 as a drying agent for aqueous work-up. H-NMR experiments were performed with a performed with a Varian Unity Inova spectrometer (Palo Alto, CA, USA) in CDCl . Proton Varian Unity Inova spectrometer (Palo Alto, CA, USA) in CDCl3. Proton chemical shifts chemical shifts were referenced to the residual CHCl signal (d = 7.26 ppm). C-NMR were referenced to the residual CHCl3 signal (δ = 7.26 ppm). C-NMR chemical shifts were chemical shifts were referenced to the solvent (d = 77.0 ppm). Abbreviations for signal referenced to the solvent (δ = 77.0 ppm). Abbreviations for signal coupling are as follows: coupling are as follows: s = singlet, d = doublet, t = triplet, m = multiplet. Coupling s = singlet, d = doublet, t = triplet, m = multiplet. Coupling constants are given in Hertz. constants are given in Hertz. IR spectrum of 5 was recorded neat with a FT-IR Nicolet IR spectrum of 5 was recorded neat with a FT-IR Nicolet 5700 spectrophotometer and is 5700 spectrophotometer and is reported in cm . The HRMS spectrum of 5 was recorded −1 reported in cm . The HRMS spectrum of 5 was recorded by infusion on Thermo LTQ by infusion on Thermo LTQ Orbitrap XL mass spectrometer (Thermo Fisher Scientific, Orbitrap XL mass spectrometer (Thermo Fisher Scientific, Waltham, MA, USA) with an Waltham, MA, USA) with an electrospray source in the positive mode, using MeOH electrospray source in the positive mode, using MeOH as solvent. as solvent. 3.2. 3.2. Synthesis of Synthesis of ((±)-((2S,5R )-((2S,5R)-5-(Acetoxymethyl)tetrahydr )-5-(Acetoxymethyl)tetrahydroofuran-2-yl)methyl furan-2-yl)methyl Be Benzoate nzoate ( (5 5) ) To a suspension of sodium periodate (2.61 g, 26.8 mmol, 2.2 equiv.) absorbed on wet sil- To a suspension of sodium periodate (2.61 g, 26.8 mmol, 2.2 equiv.) absorbed on wet ica sili(0.64 ca (0.6 mmol/g) 4 mmol/in g) i ten tr ate htra ydr hoydrof furanu /ra CH n/CH Cl 2( Cl 9:2 1 ( , 2 94 :1, 2 4 m44 L), mL), 1,5-he1,5-hexa xadiene di (1.ene 0 g, (1 12.0 .2 g, 1 mm2 o.l2 ) 2 2 was added. The mixture was cooled to 0 C and ruthenium trichloride (0.2 mol%, 244 L mmol) was added. The mixture was cooled to 0°C and ruthenium trichloride (0.2 mol%, from a 0.1 M stock solution in H O) was added dropwise to the stirred suspension. After 244 μL from a 0.1 M stock solution in H2O) was added dropwise to the stirred suspension. the complete conversion of the starting material (1 h, TLC monitoring), the reaction was After the complete conversion of the starting material (1 h, TLC monitoring), the reaction quenched by the addition of 2-propanol (excess) and the mixture was stirred for a further was quenched by the addition of 2-propanol (excess) and the mixture was stirred for a 5 min and then filtered through a sintered glass funnel. The solid was exhaustively washed further 5 min and then filtered through a sintered glass funnel. The solid was exhaustively with EtOAc and the filtrate taken to dryness to give 1.36 g (85%) of essentially pure 4 (by washed with EtOAc and the filtrate taken to dryness to give 1.36 g (85%) of essentially H-NMR) [25 1 ], as a clear oil. pure 4 (by H-NMR) [25]., as a clear oil. Benzoyl chloride (0.5 equiv., 1.64 mmol, 95 L) was added to crude 4 (217 mg, 1.64 mmol) Benzoyl chloride (0.5 equiv., 1.64 mmol, 95 μL) was added to crude 4 (217 mg, 1.64 dissolved in pyridine (1.5 mL) and the mixture was stirred at room temp. for 16 h. At this mmol) dissolved in pyridine (1.5 mL) and the mixture was stirred at room temp. for 16 h. stage, TLC analysis still revealed the presence of unreacted 4. To prevent the formation of At this stage, TLC analysis still revealed the presence of unreacted 4. To prevent the the bis-benzoylated product, the process was quenched by the addition of water (0.5 mL) formation of the bis-benzoylated product, the process was quenched by the addition of and the mixture was stirred for 15 min. and taken to dryness. The product was partitioned water (0.5 mL) and the mixture was stirred for 15 min. and taken to dryness. The product between CH Cl and water and the organic phase was washed with a sat. aqueous 2 2 was partitioned between CH2Cl2 and water and the organic phase was washed with a sat. Molbank 2022, 2022, M1349 3 of 4 NaHCO solution and then water, dried and then evaporated to give a yellow oil (163.9 mg). NMR analysis showed that this compound was essentially (>90%) the expected mono- benzoylated product. The crude obtained as above was acetylated with Ac O/pyridine overnight and taken to dryness to give a yellow oil. Purification by preparative TLC (silica, hexane/EtOAc, 1:1) afforded the bis-acylated compound 5 (183 mg, 34% for three steps) as a clear oil. –1 1 5: IR (neat) v 1745 (s), 1720 (s), 1274 (s), 1251 (shoulder), 713 (s) cm ; H-NMR max (400 MHz, CDCl ): 8.05 (2H, d, J = 8.1), 7.55 (1H, t, J = 7.5), 7.43 (2H, t, J = 7.6), 4.44–4.37 (1H, m), 4.36–4.29 (1H, m), 4.25–4.17 (1H, m), 4.05–3.98 (1H, m), 2.12–1.99 (5H, m including the acetate methyl singlet), 1.89–1.81 (2H, m), 1.79–1.71 (2H, m); C-NMR (100 MHz, CDCl ): 170.9, 166.4, 133.0, 130.0, 129.6, 128.3, 77.5, 77.4, 66.6, 66.5, 27.78, 27.76, 20.8; HRESIMS m/z: calcd. for C H O Na 301.1052 [M + Na] , found: 301.1043. 15 18 5 4. Conclusions In conclusion, a new bis-acylated cis-THF-diol product was synthesised by RuO - catalysed oxidative cyclisation of 1,5-hexadiene followed by mono-benzoylation and acety- lation. 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Molbank – Multidisciplinary Digital Publishing Institute
Published: Mar 4, 2022
Keywords: bis-acylated α-bis-hydroxymethyl-tetrahydrofuran; oxidative cyclization; 1H-NMR; 13C-NMR; FTIR; HRESIMS
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