A convenient enantioselective decarboxylative aldol reaction to access chiral α-hydroxy esters using β-keto acids

• Zhiqiang Duan,
• Jianlin Han,
• Ping Qian,
• Zirui Zhang,
• Yi Wang and
• Yi Pan

Beilstein J. Org. Chem. 2014, 10, 969–974, doi:10.3762/bjoc.10.95

• aldehydes and carboxylic acids. Other less reactive carbonyl derivatives such as isatins [11][12], ketimines [13] and sulfonylimines [14] have also been employed with β-keto acids in the decarboxylative addition processes. α-Keto esters as surrogates of aldehydes for the generation of chiral alcohols by

Addition of H-phosphonates to quinine-derived carbonyl compounds. An unexpected C9 phosphonate–phosphate rearrangement and tandem intramolecular piperidine elimination

• Łukasz Górecki,
• Artur Mucha and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 883–889, doi:10.3762/bjoc.10.85

• skeleton and a phosphorus atom. For the C9 ketones a phosphonate–phosphate rearrangement, associated with a tandem elimination of the piperidine fragment, was evidenced. Keywords: carbonyl derivatives; dialkyl phosphite addition; organophosporus; phosphonate–phosphate rearrangement; quinine oxidation

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• amount of acetaldehyde to 10% mol ratio with respect to the alkyl aromatic [58][59] (Scheme 21). Thus, while the NHPI/AQ catalytic system was particularly effective in converting alkylaromatics to the corresponding carbonyl derivatives, this approach represents a valuable alternative when hydroperoxides

Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• transition metal salts and in a very limited scope. Recently, we showed that the cheap and non-toxic main group Lewis acid MgCl2 allows smooth addition reactions of different aromatic, heteroaromatic, alkyl and benzylic zinc reagents to various carbonyl derivatives and carbon dioxide without the use of polar

Continuous gas/liquid–liquid/liquid flow synthesis of 4-fluoropyrazole derivatives by selective direct fluorination

• Jessica R. Breen,
• Graham Sandford,
• Dmitrii S. Yufit,
• Judith A. K. Howard,
• Jonathan Fray and
• Bhairavi Patel

Beilstein J. Org. Chem. 2011, 7, 1048–1054, doi:10.3762/bjoc.7.120

• manufacturing, we developed continuous flow microreactor systems that enabled gas/liquid fluorination reactions between fluorine and various substrates to occur in very efficient processes [19][20][21]. Fluoro-carbonyl derivatives can, in principle, be utilised as building blocks for the preparation of more

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

• Erwan Le Gall,
• Antoine Pignon and
• Thierry Martens

Beilstein J. Org. Chem. 2011, 7, 997–1002, doi:10.3762/bjoc.7.112

• trialled unsuccessfully, a different strategy based on the formation of solid bonds indicated that carbonyl derivatives such as acetyl chloride or methyl chloroformate were, in contrast, efficient activators of the C=N double bond, albeit used in stoichiometric amounts. This result is consistent with some

Synthetic applications of gold-catalyzed ring expansions

• David Garayalde and
• Cristina Nevado

Beilstein J. Org. Chem. 2011, 7, 767–780, doi:10.3762/bjoc.7.87

• . Upon coordination of the metal to the alkyne 59, the 1,4-dipole 61 can be formed from oxocarbenium 60. Carbonyl compounds and carbonyl derivatives, such as imines or silyl enol ethers, can also be used as dipolarophiles to generate bicyclic furans 62 in fairly good yields (Scheme 20, reaction 2

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions

• Leping Liu,
• Bo Xu and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2011, 7, 606–614, doi:10.3762/bjoc.7.71

• - or Lewis acid-catalyzed oxygen transfer from carbonyl to carbon–carbon triple bond, the so-called alkyne–carbonyl metathesis, has attracted much attention because this atom economical transformation generates α,β-unsaturated carbonyl derivatives which are of great interest in synthetic organic

• ; gold-catalyzed; oxonium; oxygen transfer; Review α,β-Unsaturated carbonyl derivatives are not only important building blocks in synthetic organic chemistry, but are also a significant motif in natural products and biologically active compounds [1][2][3][4][5][6][7][8]. The construction of the

Donor-acceptor substituted phenylethynyltriphenylenes – excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission

• Ritesh Nandy and
• Sethuraman Sankararaman

Beilstein J. Org. Chem. 2010, 6, 992–1001, doi:10.3762/bjoc.6.112

• observed in ethanol. Compounds 1d–e are carbonyl derivatives and the maximum shift in hydroxylic solvents might be due to strong hydrogen bonding interactions between the solvent and the carbonyl group in the excited state. In order to probe further the effect of solvent polarity on the emission maximum

• show strong solvatochromic emission, the reverse trend was observed. The quantum yield of fluorescence increased in DMSO compared to cyclohexane. This might be due to the increase in the viscosity of the medium which quenches the non-radiative pathways. In the cases of the carbonyl derivatives 1d and

One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

• Priyabrata Roy and
• Binay Krishna Ghorai

Beilstein J. Org. Chem. 2010, 6, No. 52, doi:10.3762/bjoc.6.52

• Priyabrata Roy Binay Krishna Ghorai Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711103, India 10.3762/bjoc.6.52 Abstract One-pot three-component coupling of o-alkynylheteroaryl carbonyl derivatives with Fischer carbene complexes and dienophiles leading to

• ] with 2-alkynyl-3-pyrazine carbonyl derivatives, followed by the generation of a hitherto unknown intermediate e.g. furo[3,4-b]pyrazine 4 and trapping of the latter with dienophiles. Phenazine derivatives can be synthesized using similar methodology from the coupling of 2-alkynyl-3-quinoxaline carbonyl

• derivative through the generation and trapping of furo[3,4-b]quinoxaline intermediates [22]. Results and Discussion Our investigation commenced with the synthesis of o-alkynyl carbonyl derivatives 1, which were prepared in good yield from the iodoketone 6A or chloroketone 6B [33] or chloroaldehyde 6C [34

Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides

• Satoru Arimitsu and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2010, 6, No. 48, doi:10.3762/bjoc.6.48

• (Scheme 3). In summary, gem-difluoro-1,7-enyne carbonyl derivatives are useful reaction partners in enyne metathesis cycloisomerization and CM–EYM tandem reactions catalyzed by ruthenium carbene complexes. The resulting diene products can be elaborated further using a Diels–Alder reaction. Comparison of

Green oxidations: Titanium dioxide induced tandem oxidation coupling reactions

• Vineet Jeena and
• Ross S. Robinson

Beilstein J. Org. Chem. 2009, 5, No. 24, doi:10.3762/bjoc.5.24

• chemistry point of view, titanium dioxide’s main use has been to oxidize alcohols to its corresponding carbonyl derivatives which has been reported many times [8][9][10]. Titanium dioxide has also been used to synthesize dihydropyrazines [11], piperazines [12], and quinoxalines [13] although in low yields

Part 1. Reduction of S-alkyl- thionocarbonates and related compounds in the presence of trialkylboranes/air

• Jean Boivin and
• Van Tai Nguyen

Beilstein J. Org. Chem. 2007, 3, No. 45, doi:10.1186/1860-5397-3-45

• ]. Secondary xanthates 7a and 8a, bearing an acetyl group, were also reduced, but in slightly lower yields (entries 6, 7). The reduction with Et3B/air is also adapted to S-alkylxanthates which are a part of fragile compounds such as ketals or carbonyl derivatives that contain a leaving group in the β-position