Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

• Alan Armstrong and
• Alexandra Ferguson

Beilstein J. Org. Chem. 2012, 8, 1747–1752, doi:10.3762/bjoc.8.199

• screen of alternative solvents, tertiary amines and bases showed that NMM and NaOH in CH2Cl2 was the optimum reagent combination for the aziridination. Having optimised our aziridination protocol for tert-butyl cinnamate, our attention then turned to examining the scope for aromatic substitution in the

Organocatalytic C–H activation reactions

• Subhas Chandra Pan

Beilstein J. Org. Chem. 2012, 8, 1374–1384, doi:10.3762/bjoc.8.159

• report by the Akiyama group is the predominant use of N,N-dibenzylamine as the amine donor in their reaction instead of cyclic tertiary amines as used by the Kim group. The present authors employed biphenyl-based chiral phosphoric acid catalysts 15a and 15b and moderate to high yields (45–95%) and

Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins

• Hang Zhang,
• Shan-Jun Zhang,
• Qing-Qing Zhou,
• Lin Dong and
• Ying-Chun Chen

Beilstein J. Org. Chem. 2012, 8, 1241–1245, doi:10.3762/bjoc.8.139

• isatins to obtain 2-oxindoles bearing a C3-quaternary chiral center, by the catalysis of chiral tertiary amines, β-isocupreidine (β-ICD) or its derivatives [23][24]. We envisaged that such a catalytic strategy should be applicable to the allylic amination of the corresponding MBH carbonates [25][26][27

• with N-benzyloxycarbonyl and O-benzyl groups [29] was applied in diethyl ether (Table 1, entry 1). Subsequently, an array of tertiary amines derived from quinidine was explored to introduce chirality into the product. While poor enantioselectivity was obtained when β-isocupreidine 1a (β-ICD) or β

Synthesis and photooxidation of styrene copolymer bearing camphorquinone pendant groups

• Branislav Husár,
• Norbert Moszner and
• Ivan Lukáč

Beilstein J. Org. Chem. 2012, 8, 337–343, doi:10.3762/bjoc.8.37

• (CQ) in the presence of H-atom donors such as ethers (H abstraction), or more efficiently tertiary amines (electron/proton transfer), is known to be an effective photoinitiator for curing methacrylate-based dental restorative resins [1][2][3][4][5][6][7][8][9]. CQ photochemistry in solution in the

Equilibrium constants and protonation site for N-methylbenzenesulfonamides

• José A. Moreira,
• Ana M. Rosa da Costa,
• Luis García-Río and
• Márcia Pessêgo

Beilstein J. Org. Chem. 2011, 7, 1732–1738, doi:10.3762/bjoc.7.203

• Hammett’s methodology is only applicable to similar classes of compounds [18][19]. In reality, during the 1950’s, a variety of acidity constants for different kinds of bases, such as tertiary amines (H0’’’) [20], amides (Ha) [21], carbinoles (HR+) [22], and indoles (HI) [23], among others [19][24], were

Reductive amination with zinc powder in aqueous media

• Giovanni B. Giovenzana,
• Daniela Imperio,
• Andrea Penoni and
• Giovanni Palmisano

Beilstein J. Org. Chem. 2011, 7, 1095–1099, doi:10.3762/bjoc.7.125

• phenolic hydroxy groups. The list illustrates the significant applicability of this one-pot zinc-mediated reductive amination. Nevertheless the protocol showed some limitations with selected substrates: i) Secondary amines failed to give tertiary amines; ii) hindered primary amines (e.g., tert-butylamine

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

• -alkylated amines in excellent yields (Scheme 21). Zeng and co-workers reported that cationic gold(I) complexes promote the addition of all types of non-tertiary amines 120 to a variety of allenes 121 to afford allylic amines 122 in good to excellent yields [58]. Importantly, the Markovnikov adduct was

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 in high yields. Primary and secondary amines also reacted with 20b to afford N-CF3 products in good yields. Tertiary amines as well as pyridines gave quaternary ammonium and pyridinium salts, respectively. Electrophilic trifluoromethylation could also be achieved by thermal decomposition of 2

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide – a tailor-made photoinitiator for dental adhesives

• Norbert Moszner,
• Iris Lamparth,
• Jörg Angermann,
• Urs Karl Fischer,
• Frank Zeuner,
• Thorsten Bock,
• Robert Liska and
• Volker Rheinberger

Beilstein J. Org. Chem. 2010, 6, No. 26, doi:10.3762/bjoc.6.26

• -butyl]acrylate [3] or 1,3-bis(methacrylamido)propane-2-yl dihydrogen phosphate (BMAMHP) [4], which show improved hydrolytic stability under acidic aqueous conditions. The visible-light (VL) photoinitiators (PIs) in current SEAs are based on mixtures of camphorquinone (CQ) and tertiary amines (A) [5

The tert- amino effect in heterocyclic chemistry: Synthesis of new fused pyrazolinoquinolizine and 1,4-oxazinopyrazoline derivatives

• Dipak Prajapati and
• Kalyan Jyoti Borah

Beilstein J. Org. Chem. 2007, 3, No. 43, doi:10.1186/1860-5397-3-43

• progress to understand the exact mechanism of the reaction. Conclusion In conclusion, we have demonstrated that N-phenyl-3-substituted pyrazolones can be used for the intramolecular alpha-cyclisation of tertiary amines [33] for the synthesis of pyrazolinoquinolizine and 1,4-oxazinopyrazoline derivatives in