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Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts

Grant number: 13/25504-1
Support type:Regular Research Grants
Duration: August 01, 2014 - July 31, 2016
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Antonio Carlos Bender Burtoloso
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

Subproject A: Synthesis of prochiral b-cetosulfoxonium ylides and its application in asymmetric insertion reactions catalyzed by gold. Subproject B: The use of Bronsted acids in the organocatalytic decomposition of diazo compounds in the presence of nucleophilic agents. (AU)

Scientific publications (14)
(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)
BERNARDIM, BARBARA; MATOS, MARIA J.; FERHATI, XHENTI; COMPANON, ISMAEL; GUERREIRO, ANA; AKKAPEDDI, PADMA; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; CORZANA, FRANCISCO; BERNARDES, GONCALO J. L. Efficient and irreversible antibody-cysteine bioconjugation using carbonylacrylic reagents. Nature Protocols, v. 14, n. 1, p. 86-99, JAN 2019. Web of Science Citations: 2.
SANTIAGO, JOAO VICTOR; BURTOLOSO, ANTONIO C. B. Synthesis of Fused Bicyclic [1,2,3]-Triazoles from gamma-Amino Diazoketones. ACS OMEGA, v. 4, n. 1, p. 159-168, JAN 2019. Web of Science Citations: 0.
ANTONIO C.B. BURTOLOSO; PATRÍCIA B. MOMO; GRAZIELE L. NOVAIS. Traditional and New methods for the Preparation of Diazocarbonyl Compounds. Anais da Academia Brasileira de Ciências, v. 90, n. 1, p. -, 2018.
BURTOLOSO, ANTONIO C. B.; MOMO, PATRICIA B.; NOVAIS, GRAZIELE L. Traditional and New methods for the Preparation of Diazocarbonyl Compounds. Anais da Academia Brasileira de Ciências, v. 90, n. 1, 1, p. 859-893, 2018. Web of Science Citations: 5.
TALERO, ALEXANDER G.; BURTOLOSO, ANTONIO C. B. Sharpless Asymmetric Dihydroxylation on ,-Unsaturated Diazoketones: A New Entry for the Synthesis of Disubstituted Furanones. Synlett, v. 28, n. 14, p. 1748-1752, SEP 2017. Web of Science Citations: 5.
DIAS, RAFAEL M. P.; MOMO, PATRICIA B.; BURTOLOSO, ANTONIO C. B. One-step syntheses of substituted 2-pyrrolidinones and 3-pyrrolidinones from alpha,beta-unsaturated diazoketones and amines. Application in the synthesis of barmumycin. Tetrahedron, v. 73, n. 26, p. 3720-3729, JUN 29 2017. Web of Science Citations: 7.
KAWAMURA, MEIRE Y.; TALERO, ALEXANDER G.; SANTIAGO, JOAO V.; GARAMBEL-VILCA, EDSON; ROSSET, ISAC G.; BURTOLOSO, ANTONIO C. B. Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-L-serinal. Journal of Organic Chemistry, v. 81, n. 21, p. 10569-10575, NOV 4 2016. Web of Science Citations: 5.
BERNARDIM, BARBARA; CAL, PEDRO M. S. D.; MATOS, MARIA J.; OLIVEIRA, BRUNO L.; MARTINEZ-SAEZ, NURIA; ALBUQUERQUE, INES S.; PERKINS, ELIZABETH; CORZANA, FRANCISCO; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; BERNARDES, GONCALO J. L. Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents. NATURE COMMUNICATIONS, v. 7, OCT 26 2016. Web of Science Citations: 31.
DIAS, RAFAEL M. P.; BURTOLOSO, ANTONIO C. B. Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of beta-Keto Thioethers. ORGANIC LETTERS, v. 18, n. 12, p. 3034-3037, JUN 17 2016. Web of Science Citations: 29.
BERNARDIM, BARBARA; COUCH, ERICA D.; HARDMAN-BALDWIN, ANDREA M.; BURTOLOSO, ANTONIO C. B.; MATTSON, ANITA E. Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds. SYNTHESIS-STUTTGART, v. 48, n. 5, p. 677-686, MAR 2016. Web of Science Citations: 11.
BURTOLOSO, ANTONIO C. B.; DIAS, RAFAEL M. P.; BERNARDIM, BARBARA. alpha,beta-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Nitrogen Heterocycles. ACCOUNTS OF CHEMICAL RESEARCH, v. 48, n. 4, p. 921-934, APR 2015. Web of Science Citations: 35.
BERNARDIM, BARBARA; HARDMAN-BALDWIN, ANDREA M.; BURTOLOSO, ANTONIO C. B. LED lighting as a simple, inexpensive, and sustainable alternative for Wolff rearrangements. RSC ADVANCES, v. 5, n. 18, p. 13311-13314, 2015. Web of Science Citations: 11.
BURTOLOSO, ANTONIO C. B.; SANTIAGO, JOAO V.; BERNARDIM, BARBARA; TALERO, ALEXANDER G. Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds. CURRENT ORGANIC SYNTHESIS, v. 12, n. 5, p. 650-659, 2015. Web of Science Citations: 6.
METZKER, GUSTAVO; BURTOLOSO, ANTONIO C. B. Conversion of levulinic acid into gamma-valerolactone using Fe-3(CO)(12): mimicking a biorefinery setting by exploiting crude liquors from biomass acid hydrolysis. CHEMICAL COMMUNICATIONS, v. 51, n. 75, p. 14199-14202, 2015. Web of Science Citations: 20.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.