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Papers by F. Javier Sardina

Research paper thumbnail of Enantiospecific Synthesis of <i>N</i>-(9-Phenylfluoren-9-yl)-α-amino Ketones

Journal of Organic Chemistry, Oct 1, 1997

Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields ... more Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-α-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-α-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-β-amino alcohols depending upon the nature of the reducing agent.

Research paper thumbnail of Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2

Journal of Organic Chemistry, Apr 1, 1986

... F. Javier Sardina, Antonio Mouriiio, and Luis Castedo* Departamento de Quimica Orgcinica, Fac... more ... F. Javier Sardina, Antonio Mouriiio, and Luis Castedo* Departamento de Quimica Orgcinica, Facultad de Quimica y Secci6n de Alcaloides del CSIC, Santiago de Compostela ... The filtrate was washed (5% HC1, H20, saturated aqueous solution of CuSO, and HzO), dried (MgSO,), ...

Research paper thumbnail of New Insights in Cyclodextrin: Surfactant Mixed Systems from the Use of Neutral and Anionic Cyclodextrin Derivatives

Journal of Physical Chemistry B, Oct 16, 2007

Research paper thumbnail of Dearomatization−Bis-alkylation of Aromatic and Heteroaromatic Diesters Promoted by Me<sub>3</sub>SnLi via a Stanna−Brook Rearrangement

Organic Letters, Feb 10, 2006

Research paper thumbnail of Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by <i>N</i>-(9-Phenylfluoren-9-yl) β-Amino Alcohols

Journal of Organic Chemistry, Mar 4, 2000

A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as cata... more A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The influence of the substituents on the stereogenic centers of the ligand has been studied, and enantioselectivities up to 97% have been obtained. Those ligands with bulky groups in the carbinol stereocenter and small groups alpha to the nitrogen atom displayed the best catalytic activity and enantioselectivity. The most enantioselective ligand (4e) was found to possess general applicability for the enantioselective addition of diethylzinc to a variety of aromatic and aliphatic aldehydes.

Research paper thumbnail of CCDC 2092000: Experimental Crystal Structure Determination

Research paper thumbnail of CCDC 1402348: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of CCDC 1876504: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of Stereoselective Synthesis of Hydrindane and Hydroazulene Derivatives by Transannular Cyclization of Nine- and Ten-Membered Carbocycles

The Journal of Organic Chemistry, 2021

Treatment of cis-fused bicyclic diene dicarboxylates with Li/naphthalene triggers a tandem ring-o... more Treatment of cis-fused bicyclic diene dicarboxylates with Li/naphthalene triggers a tandem ring-opening and transannular cyclization process that stereoselectively yields hydroazulenes and hydrindanes derivatives. Cyclononadienyl diesters, which can be isolated after the ring-opening step by judicious choice of the reaction conditions, undergo a tandem conjugate addition/intramolecular Michael addition upon treatment with chiral lithium amides to give bicyclic β-amino esters in a process where 4 contiguous stereocenters are formed with high diastereocontrol. A concise route toward the highly enantioenriched AEF ring core of the aconitine-type alkaloids has been developed as an application of this methodology. The starting cis-fused bicyclic dicarboxylates are easily prepared in one step by reductive alkylation of diisopropyl phthalate (Na/THF, followed by the appropriate bis-electrophiles).

Research paper thumbnail of Structural Elucidation of Marine Halogenated Monoterpenes by 2D-NMR and Noe Difference Spectroscopy. A Stereochemical Correction

Research paper thumbnail of ChemInform Abstract: Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

ChemInform, Aug 2, 2010

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more 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.

Research paper thumbnail of Synthesis of Deuterated Surrogate Standards for the Analysis of Legally Regulated Substances in Cosmetics

The presence of harmful substances in cosmetic products is regulated in most countries. In the Eu... more The presence of harmful substances in cosmetic products is regulated in most countries. In the European Union the Regulation (EC) No. 1223/2009 lays down the requirements for the marketing of cosmetic products. Among others, important families of compounds restricted in the Regulation are musks, allergenic fragrances and phthalates. To ensure product safety, improved analytical methods capable of reliably and reproducibly detecting the presence of traces of prohibited and/or restricted ingredients in raw materials and finished products are required. For the continuous improvement of the reliability of the analytical methods developed to check the compliance of cosmetic products with the Regulation, the use of appropriate surrogate standards or contaminants (substances that are added to the samples to be analyzed to establish the recovery and the reproducibility of the quantification of the analytes) are of utmost importance. One of the best kinds of surrogate standards are isotopica...

Research paper thumbnail of Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles

The Journal of Organic Chemistry

Research paper thumbnail of C-C bond-forming and bond-breaking processes from the reaction of diesters with Me3SnLi. Synthesis of complex bridged polycycles and di-alkyl aromatic compounds

The Journal of Organic Chemistry

Research paper thumbnail of MSpin-JCoupling. A modular program for prediction of scalar couplings and fast implementation of Karplus relationships

Magnetic Resonance in Chemistry

MSpin-JCoupling is a modular program for the prediction of scalar couplings using a large variety... more MSpin-JCoupling is a modular program for the prediction of scalar couplings using a large variety of Karplus relationships. The program was specially designed for small molecule analysis and can be run in graphical or command-line mode. The architecture of the program is highly modular, and new equations can be rapidly implemented, through a complete C++ programming interface, and deployed as run-time loadable plugins.

Research paper thumbnail of The Two Alternative Rate-Determining Steps in Benzylic Lithiation Reactions of Esters and Carbamates

Research paper thumbnail of 8-Aminomethyl-7-hydroxy-4-methylcoumarins as Multitarget Leads for Alzheimer's Disease

Research paper thumbnail of Enantiospecific Synthesis of Heterocycles from alpha-Amino Acids

Chemical Reviews, Nov 1, 1996

Research paper thumbnail of Enantiospecific Synthesis of Heterocycles from a-Amino Acids

Research paper thumbnail of Complete structural analysis of cyclic polyhalogenated monoterpenes. A force field 2-dimensional NMR study

J Org Chem, 1986

... Method B. Ketone 3 (152 mg, 1.0 mmol) yielded, after chromatography (HPLC, 1:19 ethyl ace-tat... more ... Method B. Ketone 3 (152 mg, 1.0 mmol) yielded, after chromatography (HPLC, 1:19 ethyl ace-tate/hexane), recovered fenchone 3 (152 mg ... Ricardo Riguera,*+ Ricardo A. Mosquera,i and Saulo VBzquezt Departamento de Qulmica Orghica y Seccidn de Alcaloides del CSIC and ...

Research paper thumbnail of Enantiospecific Synthesis of <i>N</i>-(9-Phenylfluoren-9-yl)-α-amino Ketones

Journal of Organic Chemistry, Oct 1, 1997

Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields ... more Enantiomerically pure N-(9-phenylfluoren-9-yl)-α-amino ketones were prepared in excellent yields by acylation of organolithium reagents with N-(9-phenylfluoren-9-yl)-α-amino acid-derived oxazolidinones. The method is not applicable for the acylation of Grignard reagents as they attack the methylenic carbon of the oxazolidinone to give the corresponding N-alkylated amino acids 13 in excellent yields. The resulting N-(9-phenylfluoren-9-yl)-α-amino ketones 8 could be stereoselectively reduced to the corresponding syn- or anti-β-amino alcohols depending upon the nature of the reducing agent.

Research paper thumbnail of Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2

Journal of Organic Chemistry, Apr 1, 1986

... F. Javier Sardina, Antonio Mouriiio, and Luis Castedo* Departamento de Quimica Orgcinica, Fac... more ... F. Javier Sardina, Antonio Mouriiio, and Luis Castedo* Departamento de Quimica Orgcinica, Facultad de Quimica y Secci6n de Alcaloides del CSIC, Santiago de Compostela ... The filtrate was washed (5% HC1, H20, saturated aqueous solution of CuSO, and HzO), dried (MgSO,), ...

Research paper thumbnail of New Insights in Cyclodextrin: Surfactant Mixed Systems from the Use of Neutral and Anionic Cyclodextrin Derivatives

Journal of Physical Chemistry B, Oct 16, 2007

Research paper thumbnail of Dearomatization−Bis-alkylation of Aromatic and Heteroaromatic Diesters Promoted by Me<sub>3</sub>SnLi via a Stanna−Brook Rearrangement

Organic Letters, Feb 10, 2006

Research paper thumbnail of Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by <i>N</i>-(9-Phenylfluoren-9-yl) β-Amino Alcohols

Journal of Organic Chemistry, Mar 4, 2000

A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as cata... more A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The influence of the substituents on the stereogenic centers of the ligand has been studied, and enantioselectivities up to 97% have been obtained. Those ligands with bulky groups in the carbinol stereocenter and small groups alpha to the nitrogen atom displayed the best catalytic activity and enantioselectivity. The most enantioselective ligand (4e) was found to possess general applicability for the enantioselective addition of diethylzinc to a variety of aromatic and aliphatic aldehydes.

Research paper thumbnail of CCDC 2092000: Experimental Crystal Structure Determination

Research paper thumbnail of CCDC 1402348: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of CCDC 1876504: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of Stereoselective Synthesis of Hydrindane and Hydroazulene Derivatives by Transannular Cyclization of Nine- and Ten-Membered Carbocycles

The Journal of Organic Chemistry, 2021

Treatment of cis-fused bicyclic diene dicarboxylates with Li/naphthalene triggers a tandem ring-o... more Treatment of cis-fused bicyclic diene dicarboxylates with Li/naphthalene triggers a tandem ring-opening and transannular cyclization process that stereoselectively yields hydroazulenes and hydrindanes derivatives. Cyclononadienyl diesters, which can be isolated after the ring-opening step by judicious choice of the reaction conditions, undergo a tandem conjugate addition/intramolecular Michael addition upon treatment with chiral lithium amides to give bicyclic β-amino esters in a process where 4 contiguous stereocenters are formed with high diastereocontrol. A concise route toward the highly enantioenriched AEF ring core of the aconitine-type alkaloids has been developed as an application of this methodology. The starting cis-fused bicyclic dicarboxylates are easily prepared in one step by reductive alkylation of diisopropyl phthalate (Na/THF, followed by the appropriate bis-electrophiles).

Research paper thumbnail of Structural Elucidation of Marine Halogenated Monoterpenes by 2D-NMR and Noe Difference Spectroscopy. A Stereochemical Correction

Research paper thumbnail of ChemInform Abstract: Enantiomerically Pure Highly Functionalized α-Amino Ketones from the Reaction of Chiral Cyclic N-(9-Phenylfluoren-9-yl) α-Amido Esters with Organolithium Reagents

ChemInform, Aug 2, 2010

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was e... more 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.

Research paper thumbnail of Synthesis of Deuterated Surrogate Standards for the Analysis of Legally Regulated Substances in Cosmetics

The presence of harmful substances in cosmetic products is regulated in most countries. In the Eu... more The presence of harmful substances in cosmetic products is regulated in most countries. In the European Union the Regulation (EC) No. 1223/2009 lays down the requirements for the marketing of cosmetic products. Among others, important families of compounds restricted in the Regulation are musks, allergenic fragrances and phthalates. To ensure product safety, improved analytical methods capable of reliably and reproducibly detecting the presence of traces of prohibited and/or restricted ingredients in raw materials and finished products are required. For the continuous improvement of the reliability of the analytical methods developed to check the compliance of cosmetic products with the Regulation, the use of appropriate surrogate standards or contaminants (substances that are added to the samples to be analyzed to establish the recovery and the reproducibility of the quantification of the analytes) are of utmost importance. One of the best kinds of surrogate standards are isotopica...

Research paper thumbnail of Bis-enolates with extended π-conjugation are powerful nucleophiles. Study of their alkylation reactions with very hindered C-electrophiles

The Journal of Organic Chemistry

Research paper thumbnail of C-C bond-forming and bond-breaking processes from the reaction of diesters with Me3SnLi. Synthesis of complex bridged polycycles and di-alkyl aromatic compounds

The Journal of Organic Chemistry

Research paper thumbnail of MSpin-JCoupling. A modular program for prediction of scalar couplings and fast implementation of Karplus relationships

Magnetic Resonance in Chemistry

MSpin-JCoupling is a modular program for the prediction of scalar couplings using a large variety... more MSpin-JCoupling is a modular program for the prediction of scalar couplings using a large variety of Karplus relationships. The program was specially designed for small molecule analysis and can be run in graphical or command-line mode. The architecture of the program is highly modular, and new equations can be rapidly implemented, through a complete C++ programming interface, and deployed as run-time loadable plugins.

Research paper thumbnail of The Two Alternative Rate-Determining Steps in Benzylic Lithiation Reactions of Esters and Carbamates

Research paper thumbnail of 8-Aminomethyl-7-hydroxy-4-methylcoumarins as Multitarget Leads for Alzheimer's Disease

Research paper thumbnail of Enantiospecific Synthesis of Heterocycles from alpha-Amino Acids

Chemical Reviews, Nov 1, 1996

Research paper thumbnail of Enantiospecific Synthesis of Heterocycles from a-Amino Acids

Research paper thumbnail of Complete structural analysis of cyclic polyhalogenated monoterpenes. A force field 2-dimensional NMR study

J Org Chem, 1986

... Method B. Ketone 3 (152 mg, 1.0 mmol) yielded, after chromatography (HPLC, 1:19 ethyl ace-tat... more ... Method B. Ketone 3 (152 mg, 1.0 mmol) yielded, after chromatography (HPLC, 1:19 ethyl ace-tate/hexane), recovered fenchone 3 (152 mg ... Ricardo Riguera,*+ Ricardo A. Mosquera,i and Saulo VBzquezt Departamento de Qulmica Orghica y Seccidn de Alcaloides del CSIC and ...