Exploring the Chemistry of Isoxazol-5-ones as Versatile Building Blocks in Organic Synthesis

• Grant number: 15/20809-4
• Support Opportunities: Regular Research Grants
• Start date: February 01, 2016
• End date: January 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Igor Dias Jurberg
• Grantee: Igor Dias Jurberg
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated research grant(s): 17/09462-8 - An aminocatalyzed stereoselective strategy for the formal alpha-propargylation of ketones, PUB.ART

Abstract

We aim to study the mechanism and design of new reactions involving isoxazol-5-ones. We will investigate reductive protocols applying these heterocycles, the preparation of new reagents, the use of chiral catalysts for the construction of enantioenriched alkynes via the addition of nucleophiles to alkylidene isoxazolones and the synthesis of fluorinated and trifluoromethylated alkynes. If successful, the methodology of trifluoromethylation will be exploited in the synthesis of a commercial drug against AIDS of proved efficiency, Efavirenz. (AU)

Scientific publications

(5)

(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)

JURBERG, IGOR D.. An Aminocatalyzed Stereoselective Strategy for the Formal alpha-Propargylation of Ketones. CHEMISTRY-A EUROPEAN JOURNAL, v. 23, n. 41, p. 9716-9720, JUL 21 2017. (15/20809-4)

STIVANIN, MATEUS L.; DUARTE, MARCELO; SARTORI, CAMILA; CAPRETI, NAYLIL M. R.; ANGOLINI, CELIO F. F.; JURBERG, IGOR D.. An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights. Journal of Organic Chemistry, v. 82, n. 19, p. 10319-10330, OCT 6 2017. (15/20809-4, 16/12749-4, 14/15718-7, 15/01331-6)

JURBERG, IGOR D.; DAVIES, HUW M. L.. Blue light-promoted photolysis of aryldiazoacetates. CHEMICAL SCIENCE, v. 9, n. 22, p. 5112-5118, JUN 14 2018. (15/20809-4)

JURBERG, IGOR D.; DAVIES, HUW M. L.. Rhodium- and Non-Metal-Catalyzed Approaches for the Conversion of Isoxazol-5-ones to 2,3-Dihydro-6H-1,3-oxazin-6-ones. ORGANIC LETTERS, v. 19, n. 19, p. 5158-5161, OCT 6 2017. (15/20809-4)

MARYASIN, BORIS; KALDRE, DAINIS; GALAVERNA, RENAN; KLOSE, IMMO; RUIDER, STEFAN; DRESCHER, MARTINA; KAEHLIG, HANSPETER; GONZALEZ, LETICIA; EBERLIN, MARCOS N.; JURBERG, IGOR D.; et al. Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a meta-selective rearrangement. CHEMICAL SCIENCE, v. 9, n. 17, p. 4124-4131, MAY 7 2018. (15/20809-4)