Team of asymmetric synthesis of nitrogen compounds

 

Slider introduccion

 

The asymmetric synthesis of nitrogen compounds team was create in 2004. The main axis of this team is the development of new asymmetric synthesis strategies aimed to obtaining chiral intermediates useful for the synthesis of compounds with various applications. The use of chiral auxiliaries that allow improve control in the generation of one or more stereogenic centers in a single stage continues to be one of the most important challenges for synthetic chemicals. It is for this reason that our efforts are focus on obtaining chiral intermediates that have incorporated a chiral auxiliary capable of directing the synthesis towards the compound of interest with the desired stereochemistry. These methods are apply to the synthesis of complex molecules with synthetic and / or biological interest

People

Dr. Jorge Juarez

Juarez-Posadas Jorge was born in Puebla, México. He completed his master’s degree in organic chemistry in 1994 and his Ph.D. degree in asymmetric organic synthesis in 1999 at the Science Institute – Benemerita Autonomous University of Puebla, working in the group of Professor Dino Gnecco. In 1997, he joined Professor Christian Marazano’s laboratories at the CNRS institute, Francia, as a visiting student working on the synthesis of pharmacologically active piperidines. Juarez-Posadas Jorge has been professor in the team of asymmetric synthesis of nitrogen compounds, science institute, center of organic – Benemerita Autonomous University of Puebla since 2001, focusing his research work on the asymmetric synthesis of bioactive piperidine compounds starting from chiral aminoalcohols.

Dra. Maria Laura Orea Flores

Orea-Flores María Laura was born in Puebla, México. She completed her master’s degree in organic chemistry in 1996 and her Ph.D. degree in asymmetric organic synthesis in 2003 at the Science Institute – Benemerita Autonomous University of Puebla, working in the group of Professor Dino Gnecco. Orea-Flores María Laura has been professor in the team of asymmetric synthesis of nitrogen compounds, Science Institute, Chemistry Center – Benemerita Autonomous University of Puebla since 2003. Her research interests are focoused on the asymmetric synthesis of nitrogen-containing molecules starting from chiral pyridin-2(1H)-one

Dr. David Aparicio

He was born in Tlaxcala, México. He completed his master’s degree in organic chemistry in 2005 and his Ph.D. degree in asymmetric synthesis in 2011 at the Science Institute – Benemerita Autonomous University of Puebla, working under supervision of Professor Joel Teran. In 2012, he joined Professor Nancy Romero’s laboratories at the Juarez Autonomous University of Tabasco, Mexico, as a postdoctoral stage working on the synthesis of pharmacologically active coumarins and arylidenes. Aparicio has been professor in the team of asymmetric synthesis of nitrogen compounds science institute, chemistry center – BUAP since 2014, focusing his research work on the total synthesis of bioactive compounds from commercially available nitrogenous chiral compounds.

Dr. Joel Luis Teran Vazquez

Terán-Vázquez Joel Luis was born in Huautla de Jiménez Oaxaca, México. He completed his Ph.D. degree in asymmetric organic synthesis in 2001 at the Science Institute – Benemerita Autonomous University of Puebla, working under supervision of Professor Dino Gnecco. In 2002, he joined Professor Laurent Micouin’s group at the University René Descartes, Paris France, as a postdoctoral stage working in the asymmetric synthesis of glycosphingolipids. Terán has been professor in the team of asymmetric synthesis of nitrogen compounds, science institute, chemistry center – Benemerita Autonomous University of Puebla since 2003, focusing his research work on the use of sulfur ylides for the production of chiral 2,3-epoxyamides and its utility on the total asymmetric synthesis of bioactive compounds. In addition, his research work is oriented to the synthesis of cyclic chiral zwitterionic compounds starting from commercially available chiral primary and secondary amines and aminoalcohols.

Dr. Angel Mendoza

Mendoza Angel was born in Mexico City, México. In 2006, he completed his Ph.D. degree in coordination chemistry, specifically in coordination chemistry of macrocyclic compounds with Pd(II), Cu(II) and Zn(II), in the Faculty of Chemistry in the National University Autonomous of Mexico (UNAM). In 2007 he start to work for the Benemerita Autonomous University of Puebla as a full time professor working in the X-ray crystallography laboratory. He would be a member of the Team of Asymmetric Synthesis of Nitrogen Compounds in 2010, supporting for crystal diffraction; solving, refining and handling crystallographic structures. Nowadays, he is interested in crystallographic field (XRD, XRF) for single crystals. As well as synthesis of 1,4-diamines (chiral and not chiral) and its interactions with transition metals.

PhD Students

Susana Morales Barba

Ramón Enrique Reyes Bravo

Ricardo López González

Manuel Velazco Ximello

Arturo Bocardo Bautista

Ulises Hernández Pareja

Ana Vargas Rodríguez

Hugo Pilotzi

Dulce Tépox Luna

Olga Hisami Rodríguez Matsui

Saúl René Torres Reyes

Postdoctoral Partnership

Mercedes Bedolla Medrano

Cristina Isabel Canché Chay

Master Students

Rodrigo Chico Merino

Alan Esau Aguilar Aguilar

Jose Carlos Palacios Rodriguez

Fredy Ramírez

Research Interest

Asymmetric synthesis of glycidic amides

Synthesis of piperidin zwitterionic type compounds

Synthesis of Chiral oxazolidines

 

Current Research

 

  • Specific synthesis of trans-2,3-epoxyamides starting from chiral oxazolidines.

  • Asymmetric tandem Conjugate addition—aldol condensation with N-acryloyloxazolidines derived from 2-phenylglycinol.

  • Synthesis of chiral zwitterionic piperidine type compounds.

 

Recent Results

 

Asymmetric Tandem Conjugate addition—aldol condensation of diethyl zinc to N-acryloyloxazolidines derived from 2-phenylglycinol and aromatic, aliphatic aldehydes and ketones..

 

Chiral cyclic zwitterionic bipyridinium-4-olates for the diastereoselective synthesis of (R,S)- and (S,R)-trozamicol.

 

7-endo cyclisation of 2,3-epoxyamides and 2,3-aziridinecarboxamides by intramolecular Friedel-Crafts reaction.

Publications

2012

Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones

Aparicio, D. M.; Gnecco, D.; Juárez, J. R.; Orea, M. L.; Mendoza, A.; Waksman, N.; Salazar, R.; Flores-Alamo, M.; Terán, J. L. Tetrahedron 2012, 68, 10252.

2013

Oxazolidine Sulfur Ylides Derived from Phenylglycinol for the Specific and Highly Diastereoselective Synthesis of Aryl and Alkyl trans-Epoxyamides

Gordillo, P. G.; Aparicio, D. M.; Flores, M.; Mendoza, A.; Orea, L.; Juárez, J. R.; Huelgas, G.; Gnecco, D.; Terán, J. L. Euro Journal of Organic Chemistry 2013, 5561.

 

Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide.

Juárez-Calderón, M.; Aparicio, D. M.; Gnecco, D.; Juárez, J. R.; Orea, L.; Mendoza, A.; Sartillo-Piscil, F.; del Olmo, E.; Terán, J. L. Tetrahedron Letters 2013, 54, 2729.

 

2014

Juárez-Calderón, M.; Aparicio, D. M.; Gnecco, D.; Juárez, J. R.; Orea, L.; Mendoza, A.; Sartillo-Piscil, F.; del Olmo, E.; Terán, J. L. Tetrahedron Letters 2013, 54, 2729.

Araceli Zárate, Laura Orea, Jorge R. Juárez, Alejandro Castro, Ángel Mendoza, Dino Gnecco and Joel L. Terán. Synthetic Communications, 44, 2838-2847, 2014. Edit.: Taylor&Francis. ISSN 0039-7911. Factor de impacto: 1.06. DOI: 10.1080/00397911.2014.918147

 

Oxidation and aromatization of the enantiopure piperidine derived from (R)-(-)-2-phenylglycinol to (1’R)-(-)-1-(2’-hydroxy-1’-phenylethyl)-1H-pyridin-2-one

Alejandro Castro,  Oscar Romero,  Joel L. Terán,  Dino Gnecco,  Laura Orea, Angel Mendoza and Jorge R. Juárez. HETEROCYCLES, Vol. 89, No. 3,  725-729, 2014 Edit. Elsevier. Japón . ISSN: 1881-0942. Factor de impacto: 1.014

http://www.heterocycles.jp/newlibrary/payments/form/23659/PDF

 

2015

7-endo cyclisation of 2,3-epoxyamides and 2,3-aziridinecarboxamides by intramolecular Friedel-Crafts reaction

Palillero-Cisneros, A.; Gordillo-Guerra, P. G.; Aparicio-Solano, D. M.; Gnecco, D.; Mendoza, A.; Juárez, J. R.; Terán J. L. Tetrahedron: Asymmetry 2015, 26, 95-101.

 

Diastereospecific etherification and diastereoselective monobromination of (R)-(-)-1-(2-hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one

Vargas, A.; Orea, M. L.; Terán, J. L.; Aparicio, D. M.; Juárez, J. R.; Enriquez, R. G.; Gnecco, D. Heterocycles 2015, 91, 1042-1047.

 

7-endo cyclisation of 2,3-epoxyamides and 2,3-aziridinecarboxamides by intramolecular Friedel-Crafts reaction

Palillero-Cisneros, A.; Gordillo-Guerra, P. G.; Aparicio-Solano, D. M.; Gnecco, D.; Mendoza, A.; Juárez, J. R.; Terán J. L. Tetrahedron: Asymmetry 2015, 26, 95-101.

 

Diastereospecific etherification and diastereoselective monobromination of (R)-(-)-1-(2-hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one

Vargas, A.; Orea, M. L.; Terán, J. L.; Aparicio, D. M.; Juárez, J. R.; Enriquez, R. G.; Gnecco, D. Heterocycles 2015, 91, 1042-1047.

 

2016

Chiral cyclic zwitterionic bipyridinium-4-olates for the diastereoselective synthesis of (R,S)- and (S,R)-trozamicol

Ricardo López-González, Araceli Zárate, David M. Aparicio, Angel Mendoza, Dino Gnecco, Jorge R. Juárez, Nancy Romero-Ceronio, Laura Orea, Joel L. Terán. Tetrahedron Letters, 2016, 57, 1683-1686. Edit. Elsevier ISSN 0040 4039. ISSN online 0040 4039. Factor de impacto 2.683

http://dx.doi.org/10.1016/j.tetlet.2016.03.029

 

Diastereoselective bromoetherification of (R)-(-)-1-(2-hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one

Anna Vargas, María L. Orea, Joel L. Terán, David M. Aparicio, Jorge R. Juárez,  Raúl G. Enriquez, and Dino Gnecco. HETEROCYCLES, 2015, 91, No. 5, 1042-1047. Edit. The Japan Institute of Heterocyclic Chemistry. Japón.  ISSN: 1881-0942 Factor de impacto: 1.014 DOI: 10.3987/COM-15-13206

 

2017

Asymmetric Tandem Conjugate Addition-Aldol Condensation with N-Acryloyloxazolidines derived from 2-Phenylglycinol

Iván Zelocualtecatl Montiel, Fernando García Alvatez, Jorge R. Juárez, Laura Orea, Dino Gnecco, Angel Mendoza, Fabrice Chemla, Franck Ferreira, Olivier Jackowski, David M. Aparicio, Alejandro Pérez Luna, and Joel L. Terán. Asian J. Org. Chem. 2017, 6, 67-70 Edit. Wiley         

ISSN: 2193-5815               ISSN electrónico: 21935807 Impact Factor: 3.275 DOI: 10.1002/ajoc.201600501

 

Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity

Marco A. Obregón-Mendoza , María Mirian Estévez-Carmona , Simón Hernández-Ortega , Manuel Soriano-García, María Teresa Ramírez-Apan, Laura Orea, Hugo Pilotzi, Dino Gnecco, Julia Cassani  and Raúl G. Enríquez Molecules 2017, 22(1), 33-46 Edit. Elsevier ISSN 1420-3049 Impact Factor: 2.749

 

2018

Highly Regioselective Ring Opening of a Common N,NDialkylAziridinium Ion by Carboxylic Acids

Ulises Hernández, Manuel Velasco, Jaime Vázquez, Joel L. Terán, Dino Gnecco, María L. Orea, David M. Aparicio, and Jorge R. Juárez*. HETEROCYCLES, 2018, Edit. The Japan Institute of Heterocyclic Chemistry. Japón. ISSN: 1881-0942

 

Diastereospecific Intramolecular Cyclopropanation of Enantiopure 8-Bromo-3-phenylhexahydrooxazolo[3,2-a]pyridin-5-ones

Anna Vargas, María L. Orea,* Dino Gnecco,* David M. Aparicio, Jorge R. Juárez, and Joel L. Terán HETEROCYCLES, 2018, Edit. The Japan Institute of Heterocyclic Chemistry. Japón.

ISSN: 1881-0942DOI: 10.3987/COM-17-13834

 

Location Map