Latest Articles of European Journal of Organic Chemistry


Design, Synthesis and preliminary biological evaluation of GlcNAc‐6P Analogues for the Modulation of Phosphoacetylglucosamine Mutase 1 (AGM1/PGM3) 10.1002/ejoc.201800183 2018-03-15 A library of GlcNAc‐6 or 1P analogues was designed and each compound was computationally evaluated through docking studies for its binding affinity to AGM1/PGM3. The compounds with the highest binding affinity ranked through a docking score, were synthesized ...
Discrimination of the Chirality of the α‐Amino Acids in Zn(II) Complexes of DPA‐Appended Binaphthyl Imine 10.1002/ejoc.201800321 2018-03-15 The binaphtholic aldehydes dangled with dipicolyl amine moieties, (R)‐1, and (R)‐2, were synthesized. The reaction of (R)‐1 with an amino acid together with ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H N...
A Highly Chemoselective Synthesis of Cyclic Divalent Propargylamines by Copper‐Catalyzed Annulation/Double A3‐Couplings 10.1002/ejoc.201800393 2018-03-15 Divalent propargylamines are a pre‐eminent class of intermediates to multidentate ligands which have wide implications for use in catalysis. Here, a highly chemoselective and versatile protocol for the construction of novel cyclic divalent propargylamines has...
Front Cover: Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-ortho-Tetrahydrocannabinols and Analogues from Natural Feedstocks (Eur. J. Org. Chem. 11/2018) 10.1002/ejoc.201800362 2018-03-15 The Front Cover shows leaves of Cannabis sativa with inverted leaf blades illustrating the synthesis of natural cannabinoid analogues, in which the pentyl side chain and the hydroxyl group on the aromatic ring are inverted with high regioselectivity. The synt...
Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-ortho-Tetrahydrocannabinols and Analogues from Natural Feedstocks 10.1002/ejoc.201800064 2018-03-15 Using a combination of Au nanoparticle-catalyzed oxidation under an O2 atmosphere and a Ti-doped montmorillonite (Ti-MMT)-catalyzed tandem arylation/double cyclization, we developed an original and highly selective method for the synthesis of ortho-tetrahydro...
Recent Advances in [CpM(III)] (M = Co, Rh, Ir)‐catalyzed intramolecular annulation through C‐H Activation 10.1002/ejoc.201800298 2018-03-14 This review aims to summarize the recent advances in the field of CpM(III) (Co, Rh, Ir)‐catalyzed C‐H activation followed by subsequent intramolecular reaction. This approach has allowed the synthesis of valuable heterocycles with high structural diversity a...
Asymmetric synthesis of new cyclic fluorinated amino‐acids 10.1002/ejoc.201800255 2018-03-14 Methodology for asymmetric synthesis of CF3‐β‐proline and CF3‐6‐membered cyclic amino acids has been developed starting from readily available N‐tert‐butanesulfinyl‐(3,3,3)‐trifluoroacetald‐imine. The Zn‐mediated allylation followed by the intramolecular 5‐en...
The EI‐MS fragmentation mechanisms of bacterial sesquiterpenes and diterpenes 10.1002/ejoc.201800217 2018-03-14 The EI‐MS fragmentation mechanisms of one bacterial sesquiterpene alcohol and four diterpene hydrocarbons were investigated using all 15 or 20 enzymatically synthesised (13C1)‐labelled isotopomers for each molecule. A position‐specific mass shift analysis (PM...
Lipid A structure and immunoinhibitory effect of the marine bacterium Cobetia pacifica KMM 3879T 10.1002/ejoc.201800279 2018-03-14 The structural elucidation of lipopolysaccharides (LPSs) from Gram‐negative marine bacteria, in addition to the assessment of their immunological properties, is a fascinating and active research field, not only because it can give insight to aid understanding...
Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines 10.1002/ejoc.201800117 2018-03-14 The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products w...

Design, Synthesis and preliminary biological evaluation of GlcNAc‐6P Analogues for the Modulation of Phosphoacetylglucosamine Mutase 1 (AGM1/PGM3)

10.1002/ejoc.201800183

2018-03-15

A library of GlcNAc‐6 or 1P analogues was designed and each compound was computationally evaluated through docking studies for its binding affinity to AGM1/PGM3. The compounds with the highest binding affinity ranked through a docking score, were synthesized ...

Discrimination of the Chirality of the α‐Amino Acids in Zn(II) Complexes of DPA‐Appended Binaphthyl Imine

10.1002/ejoc.201800321

2018-03-15

The binaphtholic aldehydes dangled with dipicolyl amine moieties, (R)‐1, and (R)‐2, were synthesized. The reaction of (R)‐1 with an amino acid together with ZnII ion produces a monomeric complex that discriminates the chirality of the bound amino acid by 1H N...

A Highly Chemoselective Synthesis of Cyclic Divalent Propargylamines by Copper‐Catalyzed Annulation/Double A3‐Couplings

10.1002/ejoc.201800393

2018-03-15

Divalent propargylamines are a pre‐eminent class of intermediates to multidentate ligands which have wide implications for use in catalysis. Here, a highly chemoselective and versatile protocol for the construction of novel cyclic divalent propargylamines has...

Front Cover: Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-ortho-Tetrahydrocannabinols and Analogues from Natural Feedstocks (Eur. J. Org. Chem. 11/2018)

10.1002/ejoc.201800362

2018-03-15

The Front Cover shows leaves of Cannabis sativa with inverted leaf blades illustrating the synthesis of natural cannabinoid analogues, in which the pentyl side chain and the hydroxyl group on the aromatic ring are inverted with high regioselectivity. The synt...

Biomimetic Cannabinoid Synthesis Revisited: Batch and Flow All-Catalytic Synthesis of (±)-ortho-Tetrahydrocannabinols and Analogues from Natural Feedstocks

10.1002/ejoc.201800064

2018-03-15

Using a combination of Au nanoparticle-catalyzed oxidation under an O2 atmosphere and a Ti-doped montmorillonite (Ti-MMT)-catalyzed tandem arylation/double cyclization, we developed an original and highly selective method for the synthesis of ortho-tetrahydro...

Recent Advances in [Cp*M(III)] (M = Co, Rh, Ir)‐catalyzed intramolecular annulation through C‐H Activation

10.1002/ejoc.201800298

2018-03-14

This review aims to summarize the recent advances in the field of Cp*M(III) (Co, Rh, Ir)‐catalyzed C‐H activation followed by subsequent intramolecular reaction. This approach has allowed the synthesis of valuable heterocycles with high structural diversity a...

Asymmetric synthesis of new cyclic fluorinated amino‐acids

10.1002/ejoc.201800255

2018-03-14

Methodology for asymmetric synthesis of CF3‐β‐proline and CF3‐6‐membered cyclic amino acids has been developed starting from readily available N‐tert‐butanesulfinyl‐(3,3,3)‐trifluoroacetald‐imine. The Zn‐mediated allylation followed by the intramolecular 5‐en...

The EI‐MS fragmentation mechanisms of bacterial sesquiterpenes and diterpenes

10.1002/ejoc.201800217

2018-03-14

The EI‐MS fragmentation mechanisms of one bacterial sesquiterpene alcohol and four diterpene hydrocarbons were investigated using all 15 or 20 enzymatically synthesised (13C1)‐labelled isotopomers for each molecule. A position‐specific mass shift analysis (PM...

Lipid A structure and immunoinhibitory effect of the marine bacterium Cobetia pacifica KMM 3879T

10.1002/ejoc.201800279

2018-03-14

The structural elucidation of lipopolysaccharides (LPSs) from Gram‐negative marine bacteria, in addition to the assessment of their immunological properties, is a fascinating and active research field, not only because it can give insight to aid understanding...

Asymmetric Organocatalysis and Photoredox Catalysis for the α-Functionalization of Tetrahydroisoquinolines

10.1002/ejoc.201800117

2018-03-14

The asymmetric α-alkylation of tetrahydroisoquinolines with cyclic ketones has been accomplished in the presence of a combined catalytic system consisting of a visible-light photoredox catalyst and a chiral primary amine organocatalyst. The desired products w...