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

• access the fluorinated compounds bearing easily removable acetyl protecting groups (Scheme 5, see Supporting Information File 1 for full experimental data). Starting from the fully hydroxylated inositols myo-3 and scyllo-3, the first step was the protection of the primary hydroxy group with trityl

• fluorination. The utilization of isopropenyl acetate as solvent in the presence of p-TSA at 80 °C for 2 h [52] gave the corresponding acetylated compounds myo-23 and scyllo-23 in good to excellent yields. The access to fluorinated compounds by nucleophilic substitution was investigated starting from these

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

• Tsuyuka Sugiishi,
• Hideki Amii,
• Kohsuke Aikawa and
• Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

• acid derivatives via carbon–carbon bond cleavage demands a high reaction temperature or basic conditions. Nevertheless, the simplicity of the operation and the reliability of higher yields would help the synthesis of fluorinated compounds in various fields. Trifluoromethylation using trifluoroacetate

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• rather poor yield (Table 3, entries 5 and 6), but the use of the ligand L1 improved the result (Table 3, entry 7). In the case of diamine 4 the yields of the corresponding products 30–32 and 34 were somewhat lower (Table 3, entries 8–11), and with fluorinated compounds we managed to isolate also

A novel family of (1-aminoalkyl)(trifluoromethyl)- and -(difluoromethyl)phosphinic acids – analogues of α-amino acids

• Natalia V. Pavlenko,
• Tatiana I. Oos,
• Yurii L. Yagupolskii,
• Igor I. Gerus,
• Uwe Doeller and
• Lothar Willms

Beilstein J. Org. Chem. 2014, 10, 722–731, doi:10.3762/bjoc.10.66

• the GABAB receptor [18]. In light of the above and in connection with our interest in the chemistry of fluorinated compounds of phosphorus we report here the preparation of a series of novel (1-aminoalkyl)phosphinic acids bearing CF3 or CHF2 groups at phosphorus. Results and Discussion Research

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

• % CuIP(OEt)3 and phenyl propargyl ether as the alkyne provided triazole-peptidomimetics 85 in 70–80% yield (Scheme 26). In a follow-up publication the same authors reported the development of tetrapeptides bearing α-CF3-α-amino and α-CF3-α-amino phosphonate cores (Scheme 27) [86]. Fluorinated compounds

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

• Tao Wang,
• Patrick Rabe,
• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311

• ; organohalogen compounds; volatiles; Introduction Today several thousands of halogenated natural products are known, most of them being produced by marine organisms [1]. The majority of halogenated natural products are chlorinated or brominated, while iodinated and particularly fluorinated compounds are

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

• Raoni S. B. Gonçalves,
• Michael Dos Santos,
• Guillaume Bernadat,
• Danièle Bonnet-Delpon and
• Benoit Crousse

Beilstein J. Org. Chem. 2013, 9, 2387–2394, doi:10.3762/bjoc.9.275

• supply a variety of organic functionalities including γ-amino alcohols [12], β-amino acids [13], β-hydroxy ketones [14][15] and β-hydroxy nitriles [14][15]. Fluorinated compounds play a central role in different branches of chemistry [16]. The incorporation of a fluorine atom into bioactive molecules

Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

• Lin Yan,
• Zhiqiang Han,
• Bo Zhu,
• Caiyun Yang,
• Choon-Hong Tan and
• Zhiyong Jiang

Beilstein J. Org. Chem. 2013, 9, 1853–1857, doi:10.3762/bjoc.9.216

• properties, compared with their parent compounds [1]. Due to the rareness of organofluorine compounds in nature, synthetic fluorinated compounds have been widely applied in numerous areas, including materials, agrochemicals, pharmaceuticals and fine chemicals [2][3][4]. In this context, the stereoselective

• conjugate addition and Mannich reaction of α-fluoro-β-ketoesters with excellent results [38][39][40]. Herein, we wish to report the first allylic alkylation of MBH carbonates with α-fluoro-β-ketoesters in excellent enantioselectivities and moderate diastereoselectivities, furnishing enantiopure fluorinated

• compounds with chiral quaternary carbon centres containing a fluorine atom. Results and Discussion In the preliminary experiments, we investigated the reaction of α-fluoro-β-ketoester 1a with MBH carbonate 2a as the model substrate, in the presence of several commercially available Cinchona alkaloids as

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

• Lukas Hintermann,
• Mauro Perseghini and
• Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

• specifically fluorinated compounds remain difficult to access because of limitations of the synthetic methodology or unpredictable reaction outcomes in the case of fluorinated starting materials. Seebach coined the term “flustrates” for “fluorinated substrates”; a term that also hints at the frustrations

Combination of gold catalysis and Selectfluor for the synthesis of fluorinated nitrogen heterocycles

• Antoine Simonneau,
• Pierre Garcia,
• Jean-Philippe Goddard,
• Virginie Mouriès-Mansuy,
• Max Malacria and
• Louis Fensterbank

Beilstein J. Org. Chem. 2011, 7, 1379–1386, doi:10.3762/bjoc.7.162

• catalysis; Selectfluor; Introduction The useful properties of fluorinated compounds in medicinal chemistry have motivated an intense effort towards the synthesis of new molecules bearing fluorine substituents [1][2]. Therefore, the development of a rapid access to C–F bonds is of great importance. Quite

Preparation, structures and preliminary host–guest studies of fluorinated syn-bis-quinoxaline molecular tweezers

• Markus Etzkorn,
• Jacob C. Timmerman,
• Matthew D. Brooker,
• Xin Yu and
• Michael Gerken

Beilstein J. Org. Chem. 2010, 6, No. 39, doi:10.3762/bjoc.6.39

• -phenylenediamine (guest [red]); host concentration: 0.01M; host–guest ratio: 1:2 (1), 1:5 (2), 1:10 (3), 1:20 (4). Fluorinated molecular tweezers. Synthesis of non-fluorinated and fluorinated syn-bis-quinoxalines. Crystallographic details for 16c and related non-fluorinated compounds. Supporting Information

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• of the 31 new chemical entities approved in 2002 contain one or several fluorine atoms. According to the World Drug Index (WDI), there are 128 fluorinated compounds with US trade names. Even more fluorinated drugs are predicted to be developed in the near future, as fluoro-organic compounds continue

• ) Thifluzamide as well as the inhibitor of acetolactate synthase (ALS) Flucarbazone-sodium. It was estimated that the number of fluorinated compounds currently under development represent some 35–50% of the all active ingredients under development [2]. One or several fluorine atoms as substituents at specific