Synthesis of butenolides and butyrolactams from sulfur ylides and diazocompounds

• Grant number: 19/12300-5
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: February 01, 2020
• End date: May 31, 2024
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Radell Echemendía Pérez
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated scholarship(s): 22/09140-9 - Organic transformation from sulfoxonium ylides and hypervalent iodine compounds, BE.EP.PD

Abstract

This research project proposes to explore the reactivity of sulfur ylides with ketenes that are generated from diazocarbonyl compounds. This combination aims to obtain functionalized ³-butenolides and butyrolactams. At first, these transformations will be evaluated in the racemic fashion and later it will be extended to the asymmetric version. Currently, there are no reports in the literature that successfully use sulfonated ylides in the reaction with diazocompounds to form poly-substituted butyrolactams and butenolides. (AU)

Scientific publications

(6)

(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)

ECHEMENDIA, RADELL; DE OLIVEIRA, KLEBER T.; BURTOLOSO, ANTONIO C. B.. Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides. ORGANIC LETTERS, v. 24, n. 35, p. 5-pg., 2022-08-26. (19/27176-8, 17/23329-9, 20/06874-6, 19/12300-5, 13/07276-1, 20/07147-0)

MOMO, PATRICIA B.; MIZOBUCHI, EDUARDO F.; ECHEMENDIA, RADELL; BADDELEY, ISABEL; GRAYSON, MATTHEW N.; BURTOLOSO, ANTONIO C. B.. Organocatalytic Enantioselective Sulfa-Michael Additions to alpha,beta-Unsaturated Diazoketones. Journal of Organic Chemistry, v. 87, n. 5, p. 9-pg., 2022-03-04. (19/12300-5, 20/07147-0, 17/23329-9, 18/02920-3, 15/22003-7)

FURNIEL, LUCAS G.; ECHEMENDIA, RADELL; BURTOLOSO, ANTONIO C. B.. Cooperative copper-squaramide catalysis for the enantioselective N-H insertion reaction with sulfoxonium ylides. CHEMICAL SCIENCE, v. 12, n. 21, p. 7453-7459, JUN 7 2021. (18/17800-3, 20/07147-0, 19/12300-5)

LEVEILLE, ALEXANDRIA N.; ECHEMENDIA, RADELL; MATTSON, ANITA E.; BURTOLOSO, ANTONIO C. B.. nantioselective Indole Insertion Reactions of alpha-Carbonyl Sulfoxonium Ylide. ORGANIC LETTERS, v. 23, n. 24, p. 9446-9450, DEC 17 2021. (20/07147-0, 17/23329-9, 19/12300-5)

ECHEMENDIA, RADELL; DE JESUS, MATHEUS P.; FURNIEL, LUCAS G.; DAY, DAVID PHILIP; BURTOLOSO, ANTONIO C. B.. Molecular Iodine Mediated Oxidation of Arylated alpha-Carbonyl Sulfoxonium Ylides to 1,2-Dicarbonyl-Containing Compounds. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 26, p. 7-pg., 2022-07-14. (18/17800-3, 19/12300-5, 20/07143-5, 20/07147-0, 19/05002-8)

DE JESUS, MATHEUS P.; ECHEMENDIA, RADELL; BURTOLOSO, ANTONIO C. B.. The alpha-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles. ORGANIC CHEMISTRY FRONTIERS, v. 10, n. 14, p. 8-pg., 2023-06-09. (19/12300-5, 20/07147-0, 20/07143-5)