Pedro Merino | University of Zaragoza (original) (raw)
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Papers by Pedro Merino
Organic & Biomolecular Chemistry
The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carrie... more The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carried out to obtain the corresponding 2-benzyl-3-(2-pyridyl)-5-hydroxymethylisoxazolidine. The influence of Lewis acids in the reaction has been studied and a complete 3,5-regioselectivity and cis diastereoselectivity was observed when the reaction was carried out with 1.0 equiv of AgOTf, [Ag(OClO3)(PPh2Me)] or Zn(OTf)2. Insight into the mechanism of the reaction has been obtained by isolating and characterizing (X-ray) the intermediate complexes. Also, a model based on both experimental and theoretical results is proposed.
Tetrahedron, 2003
A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddi... more A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddition methodology. The obtained compounds are structurally related to natural pseudouridine, where the sugar moiety is replaced by an isoxazolidine ring. Different experimental conditions, and the effect of additives on the cycloaddition process, have been examined; the best results were obtained when the cycloaddition reaction was performed
Science of Computer Programming
Science of Computer Programming
We describe the first formal specification of a non-trivial subset of MPI, the dominant communica... more We describe the first formal specification of a non-trivial subset of MPI, the dominant communication API in high performance computing. Engineering a formal specification for a non-trivial concurrency API requires the right combination of rigor, executability, ...
Nucleosides Nucleotides & Nucleic Acids, 2003
A synthetic approach towards 1′-C-branched N, O-nucleosides is reported, based on 1,3-dipolar cyc... more A synthetic approach towards 1′-C-branched N, O-nucleosides is reported, based on 1,3-dipolar cycloaddition of ethoxycarbonylnitrone. The asymmetric version of the process exploits the presence of a chiral auxiliary at the carbon atom of nitrone and leads to β-D and β-L nucleosides in good yields.
Cheminform, 1992
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Cheminform, 2009
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Journal of The Chemical Society, Chemical Communications, 1991
Current Organic Chemistry, 2009
Journal of Organic Chemistry, 1995
... Alessandro Dondoni,* Daniela Perrone, and Pedro Merino? ... 7:3 cyclohexane-EtOAc) to give pu... more ... Alessandro Dondoni,* Daniela Perrone, and Pedro Merino? ... 7:3 cyclohexane-EtOAc) to give pure N-(tert-butoxycarbonyl)-N,O-isopropylidene-L-serinol (0.78 g, 93%): ID -24.1' (C 1.4, CHC13); 'H NMR (DMSO-&, 80 "C) 6 1.42 (8, 12 H), 1.47 (6, 3 H), 3.25 (ddd, 1 H, J = 5.5, 8.5 ...
The Journal of organic chemistry, 2015
The mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT me... more The mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT methods at the M06-2X/cc-pVTZ/PCM=THF level. After the formation of a starting complex an without energy barrier, in which the lithium atom is coordinated to both nitrone and ynolate, the reaction takes place in one single kinetic step through a single transition structure. However, the formation of C-C and C-O bonds takes place sequentially through a typical two-stage, one-step process. A combined study of noncovalent interactions (NCIs) and electron localization function (ELFs) of selected points along the intrinsic reaction coordinate (IRC) of the reaction confirmed that, in the transition structure, only the C-C bond is being formed to some extent, whereas an electrostatic interaction is present between carbon and oxygen atoms previous to the formation of the C-O bond. Indeed, the formation of the second C-O bond only begins when the first C-C bond is completely formed without formatio...
Organic & Biomolecular Chemistry
The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carrie... more The cycloaddition reaction of N-benzyl C-(2-pyridyl) nitrone with allylic alcohol has been carried out to obtain the corresponding 2-benzyl-3-(2-pyridyl)-5-hydroxymethylisoxazolidine. The influence of Lewis acids in the reaction has been studied and a complete 3,5-regioselectivity and cis diastereoselectivity was observed when the reaction was carried out with 1.0 equiv of AgOTf, [Ag(OClO3)(PPh2Me)] or Zn(OTf)2. Insight into the mechanism of the reaction has been obtained by isolating and characterizing (X-ray) the intermediate complexes. Also, a model based on both experimental and theoretical results is proposed.
Tetrahedron, 2003
A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddi... more A new class of modified C-nucleosides has been synthesized according to the 1,3-dipolar cycloaddition methodology. The obtained compounds are structurally related to natural pseudouridine, where the sugar moiety is replaced by an isoxazolidine ring. Different experimental conditions, and the effect of additives on the cycloaddition process, have been examined; the best results were obtained when the cycloaddition reaction was performed
Science of Computer Programming
Science of Computer Programming
We describe the first formal specification of a non-trivial subset of MPI, the dominant communica... more We describe the first formal specification of a non-trivial subset of MPI, the dominant communication API in high performance computing. Engineering a formal specification for a non-trivial concurrency API requires the right combination of rigor, executability, ...
Nucleosides Nucleotides & Nucleic Acids, 2003
A synthetic approach towards 1′-C-branched N, O-nucleosides is reported, based on 1,3-dipolar cyc... more A synthetic approach towards 1′-C-branched N, O-nucleosides is reported, based on 1,3-dipolar cycloaddition of ethoxycarbonylnitrone. The asymmetric version of the process exploits the presence of a chiral auxiliary at the carbon atom of nitrone and leads to β-D and β-L nucleosides in good yields.
Cheminform, 1992
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Cheminform, 2009
ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Journal of The Chemical Society, Chemical Communications, 1991
Current Organic Chemistry, 2009
Journal of Organic Chemistry, 1995
... Alessandro Dondoni,* Daniela Perrone, and Pedro Merino? ... 7:3 cyclohexane-EtOAc) to give pu... more ... Alessandro Dondoni,* Daniela Perrone, and Pedro Merino? ... 7:3 cyclohexane-EtOAc) to give pure N-(tert-butoxycarbonyl)-N,O-isopropylidene-L-serinol (0.78 g, 93%): ID -24.1' (C 1.4, CHC13); 'H NMR (DMSO-&, 80 "C) 6 1.42 (8, 12 H), 1.47 (6, 3 H), 3.25 (ddd, 1 H, J = 5.5, 8.5 ...
The Journal of organic chemistry, 2015
The mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT me... more The mechanism of the reaction between nitrones and lithium ynolates has been studied using DFT methods at the M06-2X/cc-pVTZ/PCM=THF level. After the formation of a starting complex an without energy barrier, in which the lithium atom is coordinated to both nitrone and ynolate, the reaction takes place in one single kinetic step through a single transition structure. However, the formation of C-C and C-O bonds takes place sequentially through a typical two-stage, one-step process. A combined study of noncovalent interactions (NCIs) and electron localization function (ELFs) of selected points along the intrinsic reaction coordinate (IRC) of the reaction confirmed that, in the transition structure, only the C-C bond is being formed to some extent, whereas an electrostatic interaction is present between carbon and oxygen atoms previous to the formation of the C-O bond. Indeed, the formation of the second C-O bond only begins when the first C-C bond is completely formed without formatio...