Gold-catalyzed direct alkynylation of tryptophan in peptides using TIPS-EBX

• Gergely L. Tolnai,
• Jonathan P. Brand and
• Jerome Waser

Beilstein J. Org. Chem. 2016, 12, 745–749, doi:10.3762/bjoc.12.74

• alkynylation of dipeptide 4a. Supporting Information Supporting Information File 148: Experimental procedure and characterization data for all compounds. NMR spectra of new compounds. Acknowledgements We thank the EPFL for funding and F. Hoffmann-La Roche Ltd. for an unrestricted research grant. The work of

Iridium/N-heterocyclic carbene-catalyzed C–H borylation of arenes by diisopropylaminoborane

• Mamoru Tobisu,
• Takuya Igarashi and
• Naoto Chatani

Beilstein J. Org. Chem. 2016, 12, 654–661, doi:10.3762/bjoc.12.65

• ) complex bearing an ICy ligand was the most efficient catalyst. The initially formed aminoborylated products can readily be converted to the corresponding organoboron compounds bearing various boron-protecting groups. Experimental Procedure for the Ir-catalyzed borylation of heteroarenes using 1g In a

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• show any fluorine incorporation. Various types of compounds resulting from the migration of the tertiary acetate to the primary position, elimination reaction or cyclization were identified depending on the experimental procedure. From these results, the fluorination was finally investigated on myo-22

Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

• Morgan Hans,
• Jan Lorkowski,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2015, 11, 2318–2325, doi:10.3762/bjoc.11.252

• -methylphenyl)imidazolium chloride (IDip*·HCl or IPr*·HCl). Keywords: cyclization; experimental procedure; imidazolinium salt; imidazolium salt; microwave heating; Introduction Since Arduengo and co-workers successfully isolated and characterized the first imidazol-2-ylidene derivative in 1991 [1][2], stable

• , Figure 1). For each target compound, we strove to put together the most straightforward, detailed experimental procedure that was checked to afford high yield and purity, and a full characterization by 1H and 13C NMR spectroscopies. Results and Discussion Synthesis of 1,3-dicylohexylimidazolium

• ]. Furthermore, this last reagent does not lead to the formation of water, which can hydrolyze the starting diimine and has a deleterious influence on the reaction course. Thus, we adopted the experimental procedure carefully optimized by Hintermann to obtain IMes·HCl in ca. 85% yield (Scheme 5). We were also

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

• Svetlana F. Malysheva,
• Alexander V. Artem’ev,
• Nina K. Gusarova,
• Nataliya A. Belogorlova,
• Alexander I. Albanov,
• C. W. Liu and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2015, 11, 1985–1990, doi:10.3762/bjoc.11.214

• substrate scope for the aerobic addition of phosphine oxides 1a–f to vinyl sulfides 2a–c.a Supporting Information Supporting Information File 411: General remarks, experimental procedure and characterization data; crystallographic information for 3d; 1H, 13C & 31P NMR spectra of synthesized compounds

Glycoluril–tetrathiafulvalene molecular clips: on the influence of electronic and spatial properties for binding neutral accepting guests

• Yoann Cotelle,
• Marie Hardouin-Lerouge,
• Stéphanie Legoupy,
• Olivier Alévêque,
• Eric Levillain and
• Piétrick Hudhomme

Beilstein J. Org. Chem. 2015, 11, 1023–1036, doi:10.3762/bjoc.11.115

• (bromomethyl)-2-thioxo-1,3-dithiole (6) [21]. In order to determine the optimized experimental procedure to carry out the urea N-alkylation of compound 5, we took advantage from literature of previous works realized on glycoluril for such reaction using a 2,3-bis(halogenomethyl)aryl derivative. Reported

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: synthesis and characterization

• Mahabaleshwara Subrao,
• Dakshina Murthy Potukuchi,
• Girish Sharada Ramachandra,
• Poornima Bhagavath,
• Sangeetha G. Bhat and
• Srinivasulu Maddasani

Beilstein J. Org. Chem. 2015, 11, 233–241, doi:10.3762/bjoc.11.26

• changes (kJ/mol) and entropy changes (J/mol/K) of the 13a (Ph.Ox.C*Cn) series. Phase transition temperatures (°C), enthalpy changes (kJ/mol) and entropy changes (J/mol/K) of the 13b (C12Ox.C*Cn) series. Supporting Information The experimental procedure for the synthesis of 13ap–13as and 13bp–13bs with

Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines

• Praveen Reddy Adiyala,
• D. Chandrasekhar,
• Jeevak Sopanrao Kapure,
• Chada Narsimha Reddy and
• Ram Awatar Maurya

Beilstein J. Org. Chem. 2014, 10, 2065–2070, doi:10.3762/bjoc.10.214

• Information General information, general experimental procedure, characterization data of the synthesized compounds, and copies of 1H and 13C NMR spectra are given in Supporting Information File 1. Supporting Information File 514: Experimental data. Acknowledgements R.A.M. is thankful to DST-India for

Direct C–H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

• Ren Tomita,
• Yusuke Yasu,
• Takashi Koike and
• Munetaka Akita

Beilstein J. Org. Chem. 2014, 10, 1099–1106, doi:10.3762/bjoc.10.108

• laboratory. Experimental Typical NMR experimental procedure (reaction conditions in Table 1) Under N2, [Ru(bpy)3](PF6)2 (1.1 mg, 1.3 μmol), Umemoto’s reagent 1a (8.5 mg, 25 μmol), 1,1-diphenylethylene (2a, 4.3 μL, 25 μmol), SiEt4 (~1 μL) as an internal standard, and [D6]-DMSO (0.5 mL) were added to an NMR

Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

• Lisa Moni,
• Luca Banfi,
• Andrea Basso,
• Alice Brambilla and
• Renata Riva

Beilstein J. Org. Chem. 2014, 10, 209–212, doi:10.3762/bjoc.10.16

• . Synthesis of dihydrobenzoxazepinones 10. Scope of the synthesis of 2,3-dihydrobenzo[f][1,4]oxazepin-3-ones 10. Supporting Information Supporting Information File 126: Experimental procedure, characterization data and copies of 1H and 13C spectra of all new compounds. Acknowledgements We wish to thank

Synthesis of the B-seco limonoid core scaffold

• Hanna Bruss,
• Hannah Schuster,
• Rémi Martinez,
• Markus Kaiser,
• Andrey P. Antonchick and
• Herbert Waldmann

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

• were synthesized (Scheme 7; for experimental procedure see Supporting Information File 1). In the literature [50] not many examples are known in which β-alkoxy esters serve as rearrangement precursors as the β-elimination of the alkoxy group can easily occur under the rearrangement conditions. Indeed

Gold(I)-catalyzed domino cyclization for the synthesis of polyaromatic heterocycles

• Mathieu Morin,
• Patrick Levesque and
• Louis Barriault

Beilstein J. Org. Chem. 2013, 9, 2625–2628, doi:10.3762/bjoc.9.297

• important medicinally compounds. The application of this method in the total syntheses of senaequidolide (13) [26] and ellipticine (14) [27][28] are currently underway and will be reported in due course (Figure 1). Experimental General experimental procedure for the Au(I)-catalyzed cyclization: In a flask

Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide

• Sébastien Alazet,
• Kevin Ollivier and
• Thierry Billard

Beilstein J. Org. Chem. 2013, 9, 2354–2357, doi:10.3762/bjoc.9.270

• NMR with PhOCF3 as an internal standard). Reaction of phenylpiperazine (2a) with 1a under basic conditions. Supporting Information Supporting Information File 440: Experimental procedure. Acknowledgements We thank the CNRS for their financial support. The French Fluorine Network is also thanked for

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• methods with the SHELXS97 program. General experimental procedure for synthesis of pyrrole-fused isocoumarins 5 and 8: A mixture of primary amines 2 (1.5 mmol) and dihydroxy indenofurans 6 or 7 (1.0 mmol) in chloroform (5 mL) was soaked in SSA (400 mg) by stirring for 10 min and then the solvent was

Flow synthesis of phenylserine using threonine aldolase immobilized on Eupergit support

• Jagdish D. Tibhe,
• Hui Fu,
• Timothy Noël,
• Qi Wang,
• Jan Meuldijk and
• Volker Hessel

Beilstein J. Org. Chem. 2013, 9, 2168–2179, doi:10.3762/bjoc.9.254

• direct method, the enzyme was bonded directly to the surface of the support, while the indirect method a spacer is used to provide enhanced enzyme mobility. The experimental procedure for direct immobilization (Figure 9) and indirect immobilization (Figure 10) as well as enzyme retention, activity

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

• Kegong Ji,
• Jonathan Nelson and
• Liming Zhang

Beilstein J. Org. Chem. 2013, 9, 1925–1930, doi:10.3762/bjoc.9.227

• -acetoxyenones from propargyl acetates.a Supporting Information Supporting Information File 582: Experimental procedure, compound characterization, and NMR spectra. Acknowledgements The authors are grateful for the financial support from NSF (CHE-1301343).

Damage of polyesters by the atmospheric free radical oxidant NO₃^•: a product study involving model systems

• Catrin Goeschen and
• Uta Wille

Beilstein J. Org. Chem. 2013, 9, 1907–1916, doi:10.3762/bjoc.9.225

• conditions NO3• will be present in much lower concentrations compared to the polyester, our experimental procedure ensured that vulnerable sites in the polyester-model systems could be located with certainty. Due to the repeated purification by HPLC, yields could not be obtained for any of these reactions

Flow Giese reaction using cyanoborohydride as a radical mediator

• Takahide Fukuyama,
• Takuji Kawamoto,
• Mikako Kobayashi and
• Ilhyong Ryu

Beilstein J. Org. Chem. 2013, 9, 1791–1796, doi:10.3762/bjoc.9.208

• experimental procedure and supplementary experimental data. Acknowledgements This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, and Technology (MEXT), Japan. T.K. acknowledges the Research Fellowship of the Japan Society for the Promotion of

Mild and efficient cyanuric chloride catalyzed Pictet–Spengler reaction

• Ashish Sharma,
• Mrityunjay Singh,
• Nitya Nand Rai and
• Devesh Sawant

Beilstein J. Org. Chem. 2013, 9, 1235–1242, doi:10.3762/bjoc.9.140

• employed in the synthesis of a spectrum of pharmacologically active compounds on multigram to industrial scales. Experimental A typical experimental procedure: Cyanuric chloride (10 mol %) was added to the mixture of tryptamine (1) or arylamine substrate 4 (1 mmol) and aldehyde 2 (1 mmol) in DMSO at rt

A versatile and efficient approach for the synthesis of chiral 1,3-nitroamines and 1,3-diamines via conjugate addition to new (S,E)-γ-aminated nitroalkenes derived from L-α-amino acids

• Vera Lúcia Patrocinio Pereira,
• André Luiz da Silva Moura,
• Daniel Pais Pires Vieira,
• Leandro Lara de Carvalho,
• Eliz Regina Bueno Torres and
• Jeronimo da Silva Costa

Beilstein J. Org. Chem. 2013, 9, 832–837, doi:10.3762/bjoc.9.95

• , experimental procedure and spectroscopic data of 3a–c, 6a–c, 2a–c, 7b, 8a, 8b, 11a, 10b–c, 9a–b, 12a, 14a,b. Supporting Information File 6: NMR, IR and MS spectra. Acknowledgements We thank FAPERJ for the financial support and CNPq and CAPES for the fellowship for some authors. We also thank Dr C. B. Barreto

Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid

• Vladimir Lamm,
• Xiangcheng Pan,
• Tsuyoshi Taniguchi and
• Dennis P. Curran

Beilstein J. Org. Chem. 2013, 9, 675–680, doi:10.3762/bjoc.9.76

• candidates for large-scale reductions. Experimental Procedure for aldehyde reduction (examples in Scheme 2, Scheme 3, and Table 1): diMe-Imd-BH3 (1, 27.5 mg, 0.25 mmol) and acetic acid (30.0 mg, 0.50 mmol) were added to a solution of 4-bromobenzaldehyde (6, 92.5 mg, 0.50 mmol) in EtOAc (2 mL). After 24 h at

Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

• Abhishek Santra,
• Tamashree Ghosh and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 74–78, doi:10.3762/bjoc.9.9

• a flammable gas. Being operationally simple and high yielding, these reaction conditions will certainly be accepted as a useful alternative to those currently existing in this area. Experimental Typical experimental procedure To a solution of compound 1 (500 mg, 1.36 mmol) and 10% Pd(OH)2/C (50 mg

A new family of four-ring bent-core nematic liquid crystals with highly polar transverse and end groups

• Kalpana Upadhyaya,
• Venkatesh Gude,
• Golam Mohiuddin and
• Rao V. S. Nandiraju

Beilstein J. Org. Chem. 2013, 9, 26–35, doi:10.3762/bjoc.9.4

• , -(CH2)-), 1.55–1.46 (m, 2H, -(CH2)-), 0.98 (t, 3H, -CH3); Anal. calcd for C31H25ClN2O4: C, 70.92; H, 4.80; found: C, 70.61; H, 4.75. For the synthesis of 1b–1f, the same experimental procedure as described for the preparation of 1a (with appropriate chemicals as detailed in Scheme 2) was followed to

Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives

• Zhi-Cong Geng,
• Jian Chen,
• Ning Li,
• Xiao-Fei Huang,
• Yong Zhang,
• Ya-Wen Zhang and
• Xing-Wang Wang

Beilstein J. Org. Chem. 2012, 8, 1710–1720, doi:10.3762/bjoc.8.195

• experimental procedure for the cascade aza-Michael/hemiacetal reaction of disubstituted hydrazines with α,β-unsaturated aldehydes To a stirred solution of catalyst 1c or 1m (20 mol %) in CH2Cl2 or toluene (0.5 mL) was added α,β-unsaturated aldehyde 3 (1.0 equiv, 0.25 mmol) and di-substituted hydrazine 2 (1.2