Regioselective S_N2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

• Silong Xu,
• Jian Shang,
• Junjie Zhang and
• Yuhai Tang

Beilstein J. Org. Chem. 2014, 10, 990–995, doi:10.3762/bjoc.10.98

• SN2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine as an efficient synthetic method for α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction features additional advantages as mild conditions

Synthesis and stereochemical assignments of diastereomeric Ni(II) complexes of glycine Schiff base with (R)-2-(N-{2-[N-alkyl-N-(1-phenylethyl)amino]acetyl}amino)benzophenone; a case of configurationally stable stereogenic nitrogen

• Hiroki Moriwaki,
• Daniel Resch,
• Hengguang Li,
• Iwao Ojima,
• Ryosuke Takeda,
• José Luis Aceña and
• Vadim A. Soloshonok

Beilstein J. Org. Chem. 2014, 10, 442–448, doi:10.3762/bjoc.10.41

• adjusting stoichiometry or developing catalytic reactions to achieve a specific chemical and stereochemical outcome [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]. On the other hand, a measure of the value of a synthetic method, regardless of its

Triphenylene discotic liquid crystal trimers synthesized by Co₂(CO)₈-catalyzed terminal alkyne [2 + 2 + 2] cycloaddition

• Bin Han,
• Ping Hu,
• Bi-Qin Wang,
• Carl Redshaw and
• Ke-Qing Zhao

Beilstein J. Org. Chem. 2013, 9, 2852–2861, doi:10.3762/bjoc.9.321

• symmetric isomer of the 1,3,5-trisubstituted benzene was not detected, and the yield of the 1,2,4-trisubstituted isomer was almost quantitative. Therefore, we came to the conclusion that this synthetic method and the following purification procedures supplied the 1,2,4-trisubstituted benzene-cored DLC

• the central benzene core have important impacts on the supramolecular packing and phase-transition temperature. We anticipate that this Co2(CO)8-catalyzed synthetic method can be used for the synthesis of liquid crystalline polymer networks. Experimental Instruments and conditions: See Supporting

One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

• Santos Fustero,
• Paula Bello,
• Javier Miró,
• María Sánchez-Roselló,
• Günter Haufe and
• Carlos del Pozo

Beilstein J. Org. Chem. 2013, 9, 2688–2695, doi:10.3762/bjoc.9.305

• group, which involved the use of 1,7-octadiene as an internal source of ethylene. Keywords: cross metathesis; Diels–Alder; one-pot reaction; organo-fluorine; propargylic difluorides; Introduction In recent years the number of applications of olefin metathesis as a mild and competitive synthetic method

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

• isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the

A reductive coupling strategy towards ripostatin A

• Kristin D. Schleicher and
• Timothy F. Jamison

Beilstein J. Org. Chem. 2013, 9, 1533–1550, doi:10.3762/bjoc.9.175

• Prusov extended their synthetic method to syntheses of 15-deoxyripostatin A, and later ripostatin A itself [9]. All of these approaches to the ripostatins share several key features: use of ring-closing metathesis to form the 14-membered macrocycle, preceded by one or more Stille couplings to generate

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

• Helga Seyler,
• Jegadesan Subbiah,
• David J. Jones,
• Andrew B. Holmes and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

• its simple chemical structure, controlled synthetic method, reasonable spectral absorption, good semiconducting properties, high chemical stability, and wide commercial availability. Its emergence as a semiconducting material came with the development of synthetic methods that enable production of

Efficient regio- and stereoselective access to novel fluorinated β-aminocyclohexanecarboxylates

• Loránd Kiss,
• Melinda Nonn,
• Reijo Sillanpää,
• Santos Fustero and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1164–1169, doi:10.3762/bjoc.9.130

• ][60], only a relatively small number of fluorinated derivatives of this class of compounds have been synthesized so far [61][62][63][64][65][66][67][68][69][70]. Results and Discussion We recently developed a synthetic method for the regio- and stereoselective introduction of a fluorine atom onto the

Efficient synthesis of β’-amino-α,β-unsaturated ketones

• Isabelle Abrunhosa-Thomas,
• Aurélie Plas,
• Nishanth Kandepedu,
• Pierre Chalard and
• Yves Troin

Beilstein J. Org. Chem. 2013, 9, 486–495, doi:10.3762/bjoc.9.52

• synthetic method to the preparation of piperidine natural products. Experimental Organic solutions were dried over MgSO4 or Na2SO4, and filtered. When anhydrous solvents were used, they were prepared as follows: tetrahydrofuran (THF) was distilled under N2 from sodium benzophenone ketyl and used immediately

A new synthetic protocol for coumarin amino acid

• Xinyi Xu,
• Xiaosong Hu and
• Jiangyun Wang

Beilstein J. Org. Chem. 2013, 9, 254–259, doi:10.3762/bjoc.9.30

• and relatively easy to prepare this kind of fluorescent amino acid with the new synthetic method. Furthermore, it can be applied to synthesize other derivatives of the coumarin amino acid with some specific properties. Keywords: coumarin; fluorescent probe; halogen derivatives; non-natural amino acid

N-Heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed Mizoroki–Heck reaction of aryl chlorides with styrenes

• Ting-Ting Gao,
• Ai-Ping Jin and
• Li-Xiong Shao

Beilstein J. Org. Chem. 2012, 8, 1916–1919, doi:10.3762/bjoc.8.222

• ) as the ionic liquid. Keywords: aryl chloride; Mizoroki–Heck reaction; N-heterocyclic carbene; palladium complex; synthetic method; Introduction The palladium-catalyzed reaction between organic halides and alkenes, the Mizoroki–Heck reaction, is one of the most versatile methods for the formation of

A new approach toward the total synthesis of (+)-batzellaside B

• Jolanta Wierzejska,
• Shin-ichi Motogoe,
• Yuto Makino,
• Tetsuya Sengoku,
• Masaki Takahashi and
• Hidemi Yoda

Beilstein J. Org. Chem. 2012, 8, 1831–1838, doi:10.3762/bjoc.8.210

• more efficient synthetic method for the stereoselective allylation of 4 using an appropriate combination of allylic reagent and Lewis acid to produce the desired diastereomer 7 preferentially. Beginning with a reaction employing indium chloride (InCl3) instead of TBSOTf at 0 °C in dichloromethane, we

Synthesis of axially chiral oxazoline–carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe₂

• Feijun Wang,
• Shengke Li,
• Mingliang Qu,
• Mei-Xin Zhao,
• Lian-Jun Liu and
• Min Shi

Beilstein J. Org. Chem. 2012, 8, 726–731, doi:10.3762/bjoc.8.81

• amide 14a as a mixture of diastereomeric isomers successfully in 91% yield. To our delight, the two diastereomeric isomers with a chiral N-naphthyl axis, (Sa,S)-15a and (Ra,S)-15a, were synthesized from amide 14a according to the classical synthetic method for the preparation of an oxazoline ring, and

Synthesis of 2,6-disubstituted tetrahydroazulene derivatives

• Zakir Hussain,
• Henning Hopf,
• Khurshid Ayub and
• S. Holger Eichhorn

Beilstein J. Org. Chem. 2012, 8, 693–698, doi:10.3762/bjoc.8.77

• approach was reported previously [5]. Recently, a new synthetic method for the construction of a hydroazulene skeleton by a [5 + 2]cycloaddition reaction was also developed [6]. Additionally, there have been many reports on the synthesis of 2,6-disubstituted azulenes [7][8]. In 1951, the ring expansion of

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• synthetic method used to prepare the inorganic species, the presence of coligands (stabilisers) and the surface chemistry of the particular material under investigation. Furthermore, the relative ease and flexibility of synthesis of the organic ligand(s) means that their design is tailored to the particular

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

• Keith Smith,
• Gamal A. El-Hiti,
• Amany S. Hegazy and
• Benson Kariuki

Beilstein J. Org. Chem. 2011, 7, 1219–1227, doi:10.3762/bjoc.7.142

• , not only did 4 cyclize to give 7, but 5 was also in equilibrium with 4, allowing its eventual conversion into 7 and then 8. This fortuitous finding appeared to offer potential as a general synthetic method and the same lithiation procedure was therefore used with a range of other electrophiles

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• result in the formation of multi-ring products from a single substrate [149]. In 2010, a concise synthetic method for the generation of fused indoles (291–293), by a gold-catalyzed cascade cyclization of diynes 290 was developed by Hirano and co-workers [150]. The reaction gave aryl annulated[a

Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis

• Lian-jun Liu,
• Feijun Wang,
• Wenfeng Wang,
• Mei-xin Zhao and
• Min Shi

Beilstein J. Org. Chem. 2011, 7, 555–564, doi:10.3762/bjoc.7.64

• '-dimethoxybiphenyl-2,2'-diamine was treated with adamantane-2-carbonyl chloride in the presence of Et3N at room temperature (25 °C) in DCM to afford the corresponding amide (S)-1c in 71% yield. According to the synthetic method for the synthesis of compound (S)-6a, NHC–Au complex (S)-6c was successfully prepared in

The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups

• Arno Behr and
• Jessica Pérez Gomes

Beilstein J. Org. Chem. 2011, 7, 1–8, doi:10.3762/bjoc.7.1

• has become a routine and competent synthetic method for the formation of carbon–carbon double bonds [1][2][3][4][5]. Among investigations of ring opening metathesis polymerisation [6] and ring closing metathesis [7], the olefin cross-metathesis has demonstrated its great importance in providing access

Preparation of aminoethyl glycosides for glycoconjugation

• Robert Šardzík,
• Gavin T. Noble,
• Martin J. Weissenborn,
• Andrew Martin,
• Simon J. Webb and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2010, 6, 699–703, doi:10.3762/bjoc.6.81

• that aminoethyl glycosides are conveniently conjugated to surfaces containing activated carboxylates, they have become a useful generic anomeric functional group for glycoconjugation. The importance of this linker merits efforts into finding a robust synthetic method than can be used by scientists who

Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

• Norio Shibata,
• Andrej Matsnev and
• Dominique Cahard

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

• products by simple filtration or washing [20]. Since it was of interest to find an attractive synthetic method to make these reagents commercially available, Umemoto and co-workers developed a new route appropriate for the large-scale preparation of S-(trifluoromethyl)dibenzothiophenium salts. For instance

Anion receptors containing thiazine-1,1-dioxide heterocycles as hydrogen bond donors

• Hong-Bo Wang,
• James A. Wisner and
• Michael C. Jennings

Beilstein J. Org. Chem. 2010, 6, No. 50, doi:10.3762/bjoc.6.50

• potential versatility of the synthetic method described here that the elusive 2,6-disulfonamidopyridine host 4 (Figure 2) that would provide a more direct comparison to 2 is at present unknown and likely synthesized only with some difficulty. The syntheses of receptors 1 and 2 are summarized in Scheme 1. α

A practical synthesis of the ¹³C/¹⁵N- labelled tripeptide N-formyl- Met-Leu-Phe, useful as a reference in solid- state NMR spectroscopy

• Sven T. Breitung,
• Jakob J. Lopez,
• Gerd Dürner,
• Clemens Glaubitz,
• Michael W. Göbel and
• Marcel Suhartono

Beilstein J. Org. Chem. 2008, 4, No. 35, doi:10.3762/bjoc.4.35

• Wolfgang Goethe University Frankfurt, Max-von-Laue-Str. 9, D-60438 Frankfurt am Main, Germany 10.3762/bjoc.4.35 Abstract A mild synthetic method for N-formyl-Met-Leu-Phe-OH (1) is described. After Fmoc solid phase peptide synthesis, on-bead formylation and HPLC purification, more than 30 mg of the fully

Ru-catalyzed dehydrogenative coupling of carboxylic acids and silanes - a new method for the preparation of silyl ester

• Guo-Bin Liu and
• Hong-Yun Zhao

Beilstein J. Org. Chem. 2008, 4, No. 27, doi:10.3762/bjoc.4.27

• esters are formed in the case of coupling nitro-, bromo-, and chlorobenzoic acid with silanes. We believe that the Ru3(CO)12/EtI-catalyzed dehydrosilylation of carboxylic acids with silanes provides another important protocol for a one-step, highly selective, atom-economical and efficient synthetic

• method. We are currently broadening the scope of this dehydrosilylation of carboxylic acids and silanes in our laboratory and the results will be published elsewhere. Experimental To a mixture of propionic acid (40 mmol, 2.96 g), and triethylsilane (40 mmol, 4.64 g) in toluene (20 ml) was added Ru3(CO)12

One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

• Dipak Prajapati,
• Partha P. Baruah,
• Baikuntha J. Gogoi and
• Jagir S. Sandhu

Beilstein J. Org. Chem. 2006, 2, No. 5, doi:10.1186/1860-5397-2-5

• ring products 3 (Scheme 1). This mechanism explains the formation of both the products 3 &4 i.e. the presence of an aliphatic CH and loss of PhCN from M+, although they differ in their tautomeric forms. Further study of this effective synthetic method is in progress. To investigate further the