Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles

• Grant number: 13/06558-3
• Support Opportunities: Regular Research Grants
• Start date: June 01, 2013
• End date: November 30, 2015
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ricardo Samuel Schwab
• Grantee: Ricardo Samuel Schwab
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

The Asymmetric Catalysis plays a fundamental role in the construction of new chemical bonds in stereocontroled manner. There are several methodologies that allow the synthesis of enantiomerically pure compounds, among them we highlight the asymmetric metal catalyzed reactions. In this context the enantioselective addition of organozinc reagents to aldehydes and ketones in the presence of chiral ligands have received special attention, once since it is possible to obtain secondary or tertiary alcohols with high enantioselectivity, which are important precursors in the synthesis of pharmacologically and biologically active compounds. Recently, different approaches have been employed in the preparation of new poly-functionalized organozinc reagents. The low reactivity allows for the presence of many functional groups in these reagents. Many of these new reagents have been used successfully in several reactions, such as cross-coupling reactions catalyzed by palladium or nickel, acylation reactions, allylation among others. However there are few examples in the scientific literature regarding the use of these reagents in asymmetric reactions. Although the past decade has brought many advances in the preparation of new poly-functionalized organozinc reagents, it is evident that the application of these reagents in enantioselective transformations is still incipient, requiring the use of chiral ligands that can lead to formation of highly functionalized products in excellent enantiomeric excesses. In this sense, we aim to present in this project the use of these reagents in the presence of chiral ligand for the preparation of chiral functionalized alcohols and also some derivatives with biological activity. Epoxides and chiral azrididines will be also prepared by using poly-functionalized diorganozinc reagents. This project also will involve the preparation and application of new nanoparticle-supported and magnetically recoverable chiral catalyst in enantioselective addition reactions of organozinc reagents to carbonyl compounds. (AU)

Scientific publications

(24)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

DANILO Y. DE ALBUQUERQUE; WYSTAN K. O. TEIXEIRA; SENTHIL NARAYANAPERUMAL; RICARDO S. SCHWAB. Recent Developments on Palladium-Catalyzed Carbonylation Reactions in Renewable Solvents. Journal of the Brazilian Chemical Society, v. 33, n. 7, p. 637-663, 2022-06-17. (14/50249-8, 13/06558-3)

DE ALBUQUERQUE, DANILO Y.; TEIXEIRA, WYSTAN K. O.; NARAYANAPERUMAL, SENTHIL; SCHWAB, RICARDO S.. Recent Developments on Palladium-Catalyzed Carbonylation Reactions in Renewable Solvents. Journal of the Brazilian Chemical Society, v. 33, n. 8, p. 27-pg., 2022-08-01. (13/06558-3, 14/50249-8)

TEIXEIRA, WYSTAN K. O.; DE ALBUQUERQUE, DANILO YANO; NARAYANAPERUMAL, SENTHIL; SCHWAB, RICARDO S.. Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds. SYNTHESIS-STUTTGART, v. 52, n. 13, p. 1855-1873, JUL 1 2020. (14/50249-8, 13/06558-3)

DA SILVA, EVERTON M.; DE ALBUQUERQUE, DANILO YANO; ZUKERMAN-SCHPECTOR, JULIO; SCHWAB, RICARDO S.. Development of a Novel Three-step Sonogashira Cross Coupling/Deacetonation/Cycloaddition Protocol for the Synthesis of 4-aryl-1,2,3-triazoles Using 2-methyl-3-butyn-2-ol as a Versatile Acetylene Surrogate. ASIAN JOURNAL OF ORGANIC CHEMISTRY, v. 10, n. 5, MAR 2021. (14/50249-8, 13/06558-3)

CARACELLI, IGNEZ; TEIXEIRA, WYSTAN K. O.; DE ALBUQUERQUE, DANILO YANO; SCHWAB, RICARDO S.; TIEKINK, EDWARD R. T.. The crystal structure of 1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole, C14H10IN3. ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, v. 237, n. 6, p. 4-pg., 2022-09-09. (14/50249-8, 13/06558-3)

ANDRADE, FLOYD C. D.; PUGNAL, LUCAS V. B. L.; BETIM, HUGO L. I.; VANI, JESSICA F.; ZUKERMAN-SCHPECTOR, JULIO; SCHWAB, RICARDO S.. A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active alpha-Arylmethanol-1,2,3-Triazoles. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2018, n. 40, p. 5467-5476, NOV 1 2018. (14/50249-8, 13/06558-3)

DA SILVA, RODRIGO BORGES; COELHO, FELIPE LANGE; RODEMBUSCH, FABIANO SEVERO; SCHWAB, RICARDO SAMUEL; FORAIN MIOLO SCHNEIDER, JULIANA MARIA; RAMPON, DANIEL DA SILVEIRA; SCHNEIDER, PAULO HENRIQUE. Straightforward synthesis of photoactive chalcogen functionalized benzimidazo[1,2-a]quinolines. NEW JOURNAL OF CHEMISTRY, v. 43, n. 29, p. 11596-11603, AUG 7 2019. (13/06558-3)

GUERRA, RAIZA R. G.; MARTINS, FELIPE C. P.; LIMA, CAROLINA G. S.; GONCALVES, RICARDO H.; LEITE, EDSON R.; PEREIRA-FILHO, EDENIR R.; SCHWAB, RICARDO S.. Factorial design evaluation of the Suzuki cross-coupling reaction using a CrossMark magnetically recoverable palladium catalyst. Tetrahedron Letters, v. 58, n. 10, p. 903-908, MAR 8 2017. (13/06558-3, 14/50249-8)

AZEREDO, JULIANO B.; SCHWAB, RICARDO S.; BRAGA, ANTONIO L.. Synthesis of Biologically Active Selenium-Containing Molecules From Greener Perspectives. CURRENT GREEN CHEMISTRY, v. 3, n. 1, p. 51-67, 2016. (13/06558-3)

TEIXEIRA, WYSTAN K. O.; DE ALBUQUERQUE, DANILO YANO; ZUKERMAN-SCHPECTOR, JULIO; SECKLER, DIEGO; RAMPON, DANIEL S.; SCHWAB, RICARDO S.. Copper-Mediated Intramolecular Interrupted CuAAC Selanylation. Journal of Organic Chemistry, v. 88, n. 15, p. 14-pg., 2023-07-19. (14/50249-8, 21/12394-0, 13/06558-3)

CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; SCHVVAB, RICARDO S.; DA SILVA, EVERTON M.; JOTANI, MUKESH M.; TIEKINK, EDWARD R. T.. 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, v. 75, p. 11-pg., 2019-08-01. (14/50249-8, 13/06558-3)

DORNELLES, LUCIANO; RODRIGUES, OSCAR E. D.; HECK, ELISIANE F.; BENDER, CAROLINE R.; CANSIAN, MARIANE B.; SCHWAB, RICARDO S.; SEVERO FILHO, WOLMAR A.. Synthesis of 1,3,4-oxadiazole derivatives from alpha-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions. ARKIVOC, v. N/A, p. 14-pg., 2015-01-01. (13/06558-3)

CARACELLI, IGNEZ; ZUKERMAN-SCHPECTOR, JULIO; SCHVVAB, RICARDO S.; DA SILVA, EVERTON M.; JOTANI, MUKESH M.; TIEKINK, EDWARD R. T.. 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, v. 75, n. 8, p. 1232+, AUG 2019. (14/50249-8, 13/06558-3)

ZUKERMAN-SCHPECTOR, JULIO; DIAS, CASSIO DA S.; SCHWAB, RICARDO S.; JOTANI, MUKESH M.; TIEKINK, EDWARD R. T.. 4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal structure and Hirshfeld surface analysis. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, v. 74, n. 9, p. 1195+, SEP 2018. (13/06558-3, 14/50249-8)

DORNELLES, LUCIANO; RODRIGUES, OSCAR E. D.; HECK, ELISIANE F.; BENDER, CAROLINE R.; CANSIAN, MARIANE B.; SCHWAB, RICARDO S.; SEVERO FILHO, WOLMAR A.. Synthesis of 1,3,4-oxadiazole derivatives from alpha-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions. ARKIVOC, n. 7, p. 131-144, 2015. (13/06558-3)

DE ALBUQUERQUE, DANILO YANO; DE MORAES, JULIANA R.; SCHWAB, RICARDO S.. Palladium-Catalyzed Aminocarbonylation Reaction to Access 1,2,3-Triazole-5-carboxamides Using Dimethyl Carbonate as Sustainable Solvent. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 39, p. 6673-6681, OCT 24 2019. (14/50249-8, 13/06558-3)

COSTA, ELIZAMA R.; ANDRADE, FLOYD C. D.; DE ALBUQUERQUE, DANILO YANO; FERREIRA, LUANNE E. M.; LIMA, THIAGO M.; LIMA, CAROLINA G. S.; SILVA, DOMINGOS S. A.; URQUIETA-GONZALEZ, ERNESTO A.; PAIXAO, MARCIO W.; SCHWAB, RICARDO S.. Greener synthesis of 1,2,3-triazoles using a copper(i)-exchanged magnetically recoverable beta-zeolite as catalyst. NEW JOURNAL OF CHEMISTRY, v. 44, n. 35, p. 15046-15053, SEP 21 2020. (14/50249-8, 13/06558-3)

DE ALBUQUERQUE, DANILO YANO; TEIXEIRA, WYSTAN K. O.; DO SACRAMENTO, MANOELA; ALVES, DIEGO; SANTI, CLAUDIO; SCHWAB, RICARDO S.. Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source. Journal of Organic Chemistry, DEC 2021. (14/50249-8, 13/06558-3)

BORGES, RODRIGO; ANDRADE, FLOYD C. D.; SCHWAB, RICARDO S.; SOUSA, FERNANDA S. S.; DE SOUZA, MAURICE NETO; SAVEGNAGO, LUCIELLI; SCHNEIDER, PAULO H.. Straightforward synthesis and antioxidant studies of chalcogenoaziridines. Tetrahedron Letters, v. 57, n. 31, p. 3501-3504, AUG 3 2016. (13/06558-3)

CORREA, ARLENE G.; PAIXAO, MARCIO W.; SCHWAB, RICARDO S.. Application of Bio-Based Solvents in Catalysis. CURRENT ORGANIC SYNTHESIS, v. 12, n. 6, p. 675-695, 2015. (13/50680-8, 13/06558-3)

LIMA, CAROLINA G. S.; SILVA, SANDRINA; GONCALVES, RICARDO H.; LEITE, EDSON R.; SCHWAB, RICARDO S.; CORREA, ARLENE G.; PAIXAO, MARCIO W.. Highly Efficient and Magnetically Recoverable Niobium Nanocatalyst for the Multicomponent Biginelli Reaction. CHEMCATCHEM, v. 6, n. 12, p. 3455-3463, DEC 2014. (12/04986-5, 13/06558-3, 09/07281-0)

IBRAHIM, MOHAMMAD; MUSSULINI, BEN HUR M.; MORO, LUANA; DE ASSIS, ADRIANO M.; ROSEMBERG, DENIS B.; DE OLIVEIRA, DIOGO L.; ROCHA, JOAO B. T.; SCHWAB, RICARDO S.; SCHNEIDER, PAULO HENRIQUE; SOUZA, DIOGO O.; et al. Anxiolytic effects of diphenyl diselenide on adult zebrafish in a novelty paradigm. PROGRESS IN NEURO-PSYCHOPHARMACOLOGY & BIOLOGICAL PSYCHIATRY, v. 54, p. 187-194, OCT 3 2014. (13/06558-3)

DIAS, CASSIO DA S.; LIMA, THIAGO DE M.; LIMA, CAROLINA G. S.; ZUEKRMAN-SCHPECTOR, JULIO; SCHWAB, RICARDO S.. CuO Nanoparticles as An Efficient Heterogeneous Catalyst for the 1,3-Dipolar Cycloaddition of Dicarbonyl Compounds to Azides. CHEMISTRYSELECT, v. 3, n. 22, p. 6195-6202, JUN 15 2018. (17/06536-0, 13/06558-3, 14/50249-8)

ZUKERMAN-SCHPECTOR, JULIO; DIAS, CASSIO DA S.; SCHWAB, RICARDO S.; JOTANI, MUKESH M.; TIEKINK, EDWARD R. T.. 4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal structure and Hirshfeld surface analysis. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, v. 74, p. 10-pg., 2018-09-01. (14/50249-8, 13/06558-3)