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

• Grant number: 13/25504-1
• Support Opportunities: Regular Research Grants
• Start date: August 01, 2014
• End date: July 31, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Antonio Carlos Bender Burtoloso
• Host 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)

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. (13/18009-4, 13/25504-1, 15/22003-7)

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. (13/17271-7, 13/25504-1)

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. (13/18009-4, 13/25504-1, 15/22003-7)

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. (13/18009-4, 13/25504-1)

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. (12/22274-2, 13/25504-1)

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. (13/18009-4, 13/26399-7, 13/25504-1)

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; et al. Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents. NATURE COMMUNICATIONS, v. 7, OCT 26 2016. (15/07509-1, 13/25504-1, 12/22274-2)

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. (15/07509-1, 13/25504-1, 17/13168-8)

BERNARDIM, BARBARA; DUNSMORE, LAVINIA; LI, HE; HOCKING, BRAD; NUNEZ-FRANCO, REYES; NAVO, CLAUDIO D.; JIMENEZ-OSES, GONZALO; BURTOLOSO, ANTONIO C. B.; BERNARDES, GONCALO J. L.. Precise Installation of Diazo-Tagged Side-Chains on Proteins to Enable In Vitro and In-Cell Site-Specific Labeling. BIOCONJUGATE CHEMISTRY, v. 31, n. 6, p. 1604-1610, JUN 2020. (13/25504-1, 15/07509-1, 17/13168-8)

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. (13/18009-4, 13/25504-1, 17/23329-9)

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. (13/50312-9, 13/18009-4, 12/22274-2, 13/25504-1)

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. (13/18009-4, 12/22274-2, 13/25504-1)

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. (13/18009-4, 13/25504-1)

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. (12/22274-2, 13/25504-1)