Search results

Search for "Mitsunobu" in Full Text gives 123 result(s) in Beilstein Journal of Organic Chemistry.

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

  • Giovanni Picca,
  • Markus Probst,
  • Simon M. Langenegger,
  • Oleg Khorev,
  • Peter Bütikofer,
  • Anant K. Menon and
  • Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

Graphical Abstract
  • MPC-1 and MPC-2. Compound β-4Ac-Man-CEP was prepared in 4 steps from ᴅ-mannose (see Supporting Information File 1) [35][36]. Compound Cit-BZP-yne was prepared via a Mitsunobu reaction of tetrahydropyranyl (THP)-protected citronellol and a hydroxylated benzophenone derivative [10][37][38]. Compound Cit
PDF
Album
Supp Info
Full Research Paper
Published 20 Jul 2020

Recent synthesis of thietanes

  • Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

Graphical Abstract
  • -galactopyranoside (93)) from methyl α-D-glucopyranoside (90) through a Mitsunobu thioacetylation, mesylation, thioacetate hydrolysis with the treatment of sodium bicarbonate, and a subsequent intramolecular nucleophilic displacement. In the displacement step, the formation of the four-membered thietane ring is
  • 3,5-anhydro-3-thiopentofuranosides 104 from methyl α- and β-arabinosides 101 through a Mitsunobu reaction, mesylation, and hydrolysis sequence followed by an intramolecular displacement. The in situ generated thiolate nucleophilically attacked the mesylate to form the thietane ring [51] (Scheme 22
  • converted into 3,5-anhydro-3-thiopentofuranosides 135 through a Mitsunobu reaction with thiolacetic acid and hydrolysis followed by an intramolecular nucleophilic ring-opening of the oxirane ring. The newly generated thiolate underwent a nucleophilic ring-opening of the oxirane to generate the thietane ring
PDF
Album
Review
Published 22 Jun 2020

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

  • Valerian Dragutan,
  • Ileana Dragutan,
  • Albert Demonceau and
  • Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

Graphical Abstract
  • on a Diels–Alder cycloaddition, an intramolecular Mitsunobu reaction, a [3,3]-sigmatropic rearrangement, and a ring-closing metathesis. As an alternative to this approach, Clark et al. [86] efficiently performed a sequential Ru-catalyzed enyne metathesis in combination with a hydroboration, and an
  • of cyclopentene-1,4-diol that was obtained by the enzymatic desymmetrization of the corresponding diacetate, an enyne metathesis precursor was accessed by a Mitsunobu-type coupling reaction with propargylic amide. The ring-rearrangement metathesis (RRM) of this enyne precursor was carried out using
PDF
Album
Review
Published 16 Apr 2020

Copper-catalyzed O-alkenylation of phosphonates

  • Nuria Vázquez-Galiñanes,
  • Mariña Andón-Rodríguez,
  • Patricia Gómez-Roibás and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56

Graphical Abstract
  • procedures involving a Mitsunobu reaction between 2-hydroxyalkyl phenyl selenides and phosphonic acid monoesters followed by an oxidation/elimination step [14] or reaction of an enolate with a phosphonic dichloride and subsequent treatment with an alcohol [15] (Scheme 1a). However, these procedures are
PDF
Album
Supp Info
Letter
Published 03 Apr 2020

Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol

  • María C. Mollo,
  • Natalia B. Kilimciler,
  • Juan A. Bisceglia and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2020, 16, 32–38, doi:10.3762/bjoc.16.5

Graphical Abstract
  • reactions in either case. The synthesis of 2-phenyl-4,5,6,7-tetrahydro-1,3-thiazepine by cyclodehydration of N-(4-hydroxybutyl)thiobenzamide was attempted with different condensing agents: PPA (100 °C, 15 h), Burgess (25 °C, 48 h) and PEG-Burgess (80 °C, 2 h) reagents, and under Mitsunobu conditions. In the
  • Mitsunobu conditions led exclusively to the pyrrolidine derivative (76%) [32]. Therefore, the few literature examples reported until now are either complicated by side reactions or involve long reaction times and/or modest yields. Polyphosphoric acid (PPA) esters PPE (ethyl polyphosphate) and PPSE
  • -thiobenzoylaminobutanol with PEG-linked Burgess reagent and under Mitsunobu conditions led to significant amounts of N-thiobenzoylpyrrolidine [32]. In fact, this kinetically favoured competitive reaction also occurs in the closely related cyclization of N-benzoylaminobutanol with PPSE, which leads exclusively to N
PDF
Album
Supp Info
Full Research Paper
Published 06 Jan 2020

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

  • Anna Kmieciak and
  • Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

Graphical Abstract
  • chromatography on silica gel. For the purpose of this study, (1R,4R,5R)-apopinenol (16) was subjected to the Mitsunobu reaction to obtain the product with inverted configuration at C4. Alcohol 16 was reacted with diisopropyl azodicarboxylate, triphenylphosphine, and p-nitrobenzoic acid in THF [30]. 1H NMR
PDF
Album
Supp Info
Full Research Paper
Published 22 Oct 2019

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

  • Iwona E. Głowacka,
  • Aleksandra Trocha,
  • Andrzej E. Wróblewski and
  • Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

Graphical Abstract
  • to synthesize the natural (2S,3R,4R,5R)-184 the lactone 186b was subjected to Mitsunobu reaction followed by the ester reduction and the hydrogenolytic cleavage of the 1-phenylethyl group. Piperidines: A cis-disubstituted piperidine scaffold was identified in several piperidine alkaloids of diverse
PDF
Album
Review
Published 23 Jul 2019

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

  • Małgorzata Urbańczyk,
  • Michał Jewgiński,
  • Joanna Krzciuk-Gula,
  • Jerzy Góra,
  • Rafał Latajka and
  • Norbert Sewald

Beilstein J. Org. Chem. 2019, 15, 1581–1591, doi:10.3762/bjoc.15.162

Graphical Abstract
  • amino groups of the resin were o-NBS protected by treatment of 4-nitrobenzenesulfonyl chloride (o-NBS-Cl) and sym-collidine in NMP (Scheme 1A, b). Subsequently the resin was N-methylated by Mitsunobu reaction (Scheme 1A, c). Triphenylphosphine (PPh3) was dissolved in dry THF and methanol and shaken with
PDF
Album
Supp Info
Full Research Paper
Published 16 Jul 2019

Strong hyperconjugative interactions limit solvent and substituent influence on conformational equilibrium: the case of cis-2-halocyclohexylamines

  • Camila B. Francisco,
  • Cleverton S. Fernandes,
  • Ulisses Z. de Melo,
  • Roberto Rittner,
  • Gisele F. Gauze and
  • Ernani A. Basso

Beilstein J. Org. Chem. 2019, 15, 818–829, doi:10.3762/bjoc.15.79

Graphical Abstract
  • -Fluorocyclohexanol was prepared according the literature [36] to provide cis-2-fluorocyclohexylamine. cis-2-Fluorocyclohexylamine (F) was obtained by a Mitsunobu–Gabriel reaction, as described by Thvedt and co-workers [37]. Under nitrogen atmosphere, trans-2-fluorocyclohexanol (6.00 mmol), triphenylphosphine (6.60
PDF
Album
Supp Info
Full Research Paper
Published 01 Apr 2019

Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling

  • Jan Hendrik Lang and
  • Thomas Lindel

Beilstein J. Org. Chem. 2019, 15, 577–583, doi:10.3762/bjoc.15.53

Graphical Abstract
  • propionyl chloride/pyridine, 85%) instead of 9 gave a quantitative yield of the hydroxy ester 12, but a lower dr (4:1). For both cases, we inverted the carbinol centre by Mitsunobu reaction employing p-methoxyphenol. DEAD was used instead of DIAD because of facilitated purification. It was possible to
  • . The synthesis of photoreactive tripeptide analogues incorporating photo amino acids 4–6 will be explored thereafter. Actin-binding cyclodepsipeptides, photo amino acids, retrosynthetic cuts of polyketide 7 leading to organozinc compound 8. Synthesis of γ-hydroxy esters 11 and 12, followed by Mitsunobu
PDF
Album
Supp Info
Full Research Paper
Published 28 Feb 2019

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

  • Seema V. Kanojia,
  • Sucheta Chatterjee,
  • Subrata Chattopadhyay and
  • Dibakar Goswami

Beilstein J. Org. Chem. 2019, 15, 490–496, doi:10.3762/bjoc.15.42

Graphical Abstract
  • offset the limitations of a resolution-based protocol, (R)-5 was hydrolyzed with alcoholic KOH to furnish (R)-4 (Scheme 1). Its inversion under the Mitsunobu conditions (Ph3P/DIAD/p-nitrobenzoic acid/THF; KOH/EtOH/25 °C/8 h, 91% over two steps) gave (S)-4 [46]. The benzylation of the hydroxy function in
  • of most active HPA-12 isomers, originally proposed (1) and revised (2). Lipase-catalyzed trans-acylation of (±)-4 and subsequent Mitsunobu inversion. Conditions: (i) Zn/THF/allyl bromide/aqueous sat. NH4Cl/25 °C/3 h; (ii) vinyl acetate/lipase (Table 1); (iii) KOH/EtOH/25 °C/6 h; (iv) Ph3P/DIAD/p
PDF
Album
Supp Info
Full Research Paper
Published 18 Feb 2019

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

  • Andrejs Šišuļins,
  • Jonas Bucevičius,
  • Yu-Ting Tseng,
  • Irina Novosjolova,
  • Kaspars Traskovskis,
  • Ērika Bizdēna,
  • Huan-Tsung Chang,
  • Sigitas Tumkevičius and
  • Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

Graphical Abstract
  • available 2,6-dichloropurine (1a) by subsequent alkylation of the N(9) position and azido group introduction in C(2) and C(6) positions. The N(9) position of purine was alkylated in two different ways: 1) using alkyl halides in the presence of a strong base, and 2) using alcohols under Mitsunobu conditions
  • times. For example, in the case of 1-bromododecane, the reaction required 72 hours to complete. On the other hand, Mitsunobu reaction (method B, Scheme 1) was performed between the corresponding alcohol and 2,6-dichloropurine in anhydrous THF at 0–20 °C for 1–1.5 h, resulting in average yields of 66
PDF
Album
Supp Info
Full Research Paper
Published 15 Feb 2019

Synthesis of nonracemic hydroxyglutamic acids

  • Dorota G. Piotrowska,
  • Iwona E. Głowacka,
  • Andrzej E. Wróblewski and
  • Liwia Lubowiecka

Beilstein J. Org. Chem. 2019, 15, 236–255, doi:10.3762/bjoc.15.22

Graphical Abstract
  • -hydroxyglutamate [(2S,4R)-81] (Scheme 20) [82]. To synthesize (2S,4S)-81 the inversion of configuration at C4 executed by Mitsunobu reaction preceded oxidation at C5 and the ring opening [82]. O-Benzyl ethers of (2S,4R)-3 and (2S,4S)-3 were prepared by the same methodology [50]. Another approach to the
  • intramolecular lactonization to form 83 by implementation of the Mitsunobu reaction. After opening of the lactone ring with trichloroethanol and silylation of the hydroxy group oxidation at C5 was performed in the usual way to give a pyroglutamate 84. Benzyl or p-methoxybenzyl esters 85a or 85b were next
PDF
Album
Review
Published 25 Jan 2019

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

  • Pierre-Antoine Nocquet,
  • Aurélie Macé,
  • Frédéric Legros,
  • Jacques Lebreton,
  • Gilles Dujardin,
  • Sylvain Collet,
  • Arnaud Martel,
  • Bertrand Carboni and
  • François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

Graphical Abstract
  • configuration of the stereogenic center bearing the hydroxy group (Scheme 5). With this in mind, the secondary alcohol 23 was engaged in a Mitsunobu reaction using p-nitrobenzoic acid as nucleophile to afford the expected compound 25. Hydrolysis of the ester was achieved using potassium carbonate in methanol to
PDF
Album
Supp Info
Full Research Paper
Published 29 Nov 2018

Synthesis of pyrrolidine-based hamamelitannin analogues as quorum sensing inhibitors in Staphylococcus aureus

  • Jakob Bouton,
  • Kristof Van Hecke,
  • Reuven Rasooly and
  • Serge Van Calenbergh

Beilstein J. Org. Chem. 2018, 14, 2822–2828, doi:10.3762/bjoc.14.260

Graphical Abstract
  • functionalized side chains are introduced prior to coupling and ring closure to afford 8. This new synthetic route would be more convergent and efficient for the preparation of 3. Retrosynthetic analysis led to 9 and 10 as two key synthons, which would be assembled via a Mitsunobu–Fukuyama reaction, and
  • nucleophile [22][23]. Attempts to substitute the alcohol functionality of 12 via displacement of the derived mesylate with NaN3 failed, similar to previously reported difficulties by Trost et al. [24]. The benzamide substituent was therefore introduced via Mitsunobu reaction with N-Boc-protected ortho
  • -propanediol (16), which was selectively monoprotected in high yield as TBS ether (Scheme 3) [25]. The remaining alcohol was then substituted for a phthalimide via Mitsunobu reaction. Phthalimide deprotection, acylation with benzoic acid, and removal of the silyl protecting group furnished 10. Fragments 9 and
PDF
Album
Supp Info
Full Research Paper
Published 12 Nov 2018

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

  • Maroš Bella,
  • Sergej Šesták,
  • Ján Moncoľ,
  • Miroslav Koóš and
  • Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

Graphical Abstract
  • ). In order to obtain final compounds 5, a configurational inversion of the stereocenter at C-5 in 18 was necessary. The inversion of the configuration was first attempted by a modified Mitsunobu reaction or activation of the hydroxy group by mesylation according to Trajkovic et al. [34]. However, these
PDF
Album
Supp Info
Full Research Paper
Published 17 Aug 2018

Anomeric modification of carbohydrates using the Mitsunobu reaction

  • Julia Hain,
  • Patrick Rollin,
  • Werner Klaffke and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

Graphical Abstract
  • 238 417281 Haus der Technik e.V., Hollestr. 1, 45127 Essen, Germany, Fax: +49 201 1803269 10.3762/bjoc.14.138 Abstract The Mitsunobu reaction basically consists in the conversion of an alcohol into an ester under inversion of configuration, employing a carboxylic acid and a pair of two auxiliary
  • glycosciences. Therefore, this review focuses on the use of the Mitsunobu reaction for modifications of sugar hemiacetals. Strikingly, unprotected sugars can often be converted regioselectively at the anomeric center, whereas in other cases, the other hydroxy groups in reducing sugars have to be protected to
  • achieve good results in the Mitsunobu procedure. We have reviewed on the one hand the literature on anomeric esterification, including glycosyl phosphates, and on the other hand glycoside synthesis, including S- and N-glycosides. The mechanistic details of the Mitsunobu reaction are discussed as well as
PDF
Album
Review
Published 29 Jun 2018

Recent applications of chiral calixarenes in asymmetric catalysis

  • Mustafa Durmaz,
  • Erkan Halay and
  • Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

Graphical Abstract
  • calixarenes and their catalytic performances in the asymmetric Suzuki–Miyaura coupling and Tsuji–Trost allylic alkylation reactions (Scheme 7) [42]. Calix[4]arene mono and dithiophosphines 24–26 were efficiently synthesized from p-tert-butylcalix[4]arene by a one pot Mitsunobu alkylation using
PDF
Album
Review
Published 08 Jun 2018

Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

  • Karolina Tiara,
  • Mykhaylo A. Potopnyk and
  • Sławomir Jarosz

Beilstein J. Org. Chem. 2018, 14, 634–641, doi:10.3762/bjoc.14.50

Graphical Abstract
  • alternative way to the desired amine 12a, based on the SN2 reaction of the activated alcohol 13 [34][35] with benzylamine, also failed (Scheme 2). The Mitsunobu approach to convert the hydroxy group into an amine function was also unsuccessful. Although 13 reacted with phthalimide gave the desired product 13a
  • of alcohol 13 (derived from D-glucose) with a rigid fragment and we decided to introduce the phenyl ring. Treatment of alcohol 13 with para-nitrophenol under Mitsunobu conditions afforded the nitro compound 14 in 63% yield. Stereoisomeric alditol 15, obtained from D-mannose, was converted analogously
PDF
Album
Supp Info
Full Research Paper
Published 15 Mar 2018

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

  • Ranjana Aggarwal and
  • Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Graphical Abstract
  • . The reaction of 5-amino-4-cyanopyrazole (208) and formamide was carried out by Todorovic et al. [136] under microwave irradiation at 200 °C to give 4-aminopyrazolo[3,4-d]pyrimidine (223) which on iodination with N-iodosuccinimide followed by N1-alkylation (Mitsunobu or substitution) provided
PDF
Album
Review
Published 25 Jan 2018

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres

  • Myriam Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2017, 13, 2637–2658, doi:10.3762/bjoc.13.262

Graphical Abstract
  • -fluoro-2-phosphonoacetate (1) was converted into the α-fluoro-α,β-unsaturated carbonyl 3 using the HWE olefination. The (Z)-isomer was obtained with complete selectivity. Then, reduction of the ester into the corresponding alcohol followed by a Mitsunobu reaction allowed the insertion of the NH
  • . This was then converted into a protected amino group employing a Mitsunobu reaction. Finally, removal of the nosyl group, followed by hydrolysis using lithium hydroxide, afforded the targeted isostere 24. Sano and co-workers also worked on the Mg(II)-promoted stereoselective synthesis of (Z
  • methyl ester using trimethylsilyldiazomethane, followed by its reduction to the corresponding alcohol and a Mitsunobu reaction, permitted the incorporation of the N-terminal moiety. Then, removal of the Ns group of 28 and deprotection of the primary alcohol was performed to obtain 29 which underwent a
PDF
Album
Review
Published 12 Dec 2017

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

  • Raju Cheerlavancha,
  • Ahmed Ahmed,
  • Yun Cheuk Leung,
  • Aggie Lawer,
  • Qing-Quan Liu,
  • Marina Cagnes,
  • Hee-Chan Jang,
  • Xiang-Guo Hu and
  • Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

Graphical Abstract
  • modify the synthesis shown in Scheme 4 to produce the all-syn trifluoroalkane 40b. Thus, the alcohol 37 underwent a Mitsunobu-type inversion of configuration, and O’Hagan’s series of three consecutive fluorination reactions [34] were subsequently applied to successfully deliver the all-syn
PDF
Album
Supp Info
Full Research Paper
Published 01 Nov 2017

Synthesis of benzannelated sultams by intramolecular Pd-catalyzed arylation of tertiary sulfonamides

  • Valentin A. Rassadin,
  • Mirko Scholz,
  • Anastasiia A. Klochkova,
  • Armin de Meijere and
  • Victor V. Sokolov

Beilstein J. Org. Chem. 2017, 13, 1932–1939, doi:10.3762/bjoc.13.187

Graphical Abstract
  • precursor 20 was prepared in one step from the respective sulfonamide 19 and 2-iodobenzyl alcohol employing a Mitsunobu protocol (Scheme 6) [49]. Treatment of 20 with palladium acetate, Ph3P, and sodium hydride in dioxane at 90 °С for 20 h furnished the target sultam 21 in 49% yield. Apparently, the
PDF
Album
Supp Info
Full Research Paper
Published 12 Sep 2017

The chemistry and biology of mycolactones

  • Matthias Gehringer and
  • Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

Graphical Abstract
PDF
Album
Review
Published 11 Aug 2017

New electroactive asymmetrical chalcones and therefrom derived 2-amino- / 2-(1H-pyrrol-1-yl)pyrimidines, containing an N-[ω-(4-methoxyphenoxy)alkyl]carbazole fragment: synthesis, optical and electrochemical properties

  • Daria G. Selivanova,
  • Alexei A. Gorbunov,
  • Olga A. Mayorova,
  • Alexander N. Vasyanin,
  • Igor V. Lunegov,
  • Elena V. Shklyaeva and
  • Georgii G. Abashev

Beilstein J. Org. Chem. 2017, 13, 1583–1595, doi:10.3762/bjoc.13.158

Graphical Abstract
  • -disubstituted 2-(pyrrol-1-yl)pyrimidine via Clausson–Kaas condensation (8). Alkylation of 4-methoxyphenol was realized with the help of the traditional base-catalyzed O-alkylation process in acetone media [11]. N-Alkylated carbazole derivatives can be obtained by different methods such as Mitsunobu reaction [12
PDF
Album
Supp Info
Full Research Paper
Published 10 Aug 2017
Other Beilstein-Institut Open Science Activities