Exploring the application of diazocarbonyl compounds and sulfur ylides in the asymmetric ring opening reactions with epoxides for the synthesis of oxetanes and functionalized alcohols

• Grant number: 17/23837-4
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: March 01, 2018
• End date: December 31, 2022
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Clarice Alves Dale Caiuby
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated scholarship(s): 20/11955-5 - Imidoyl sulfoxonium ylides as new precursors of a-imino metal-carbene complexes in organic synthesis, BE.EP.DR

Abstract

A great challenge for synthetic organic chemists is ensuring molecular diversity and structural complexity in reaction products, carried out by selective methodologies with a few number of steps. The development of synthetic approaches that provide enantiomerically enriched compounds have attracted a continuous interest from both academia and industry, since different enantiomers of an organic molecule can exhibit distinct biological activities. In this context, this research project proposes to explore the nucleophilicity of diazocarbonyl compounds and sulfur ylides in the ring opening of epoxides promoted by Lewis acids and organocatalysts (aiming the construction of functionalized alcohols and oxetanes). In a first moment, these transformations will be performed in a non-asymmetric mode and, later, extended to an asymmetric version. Moreover, there are no reports that successfully use functionalized sulfur ylides in the opening of racemic epoxides to provide enantiomerically enriched oxetanes. In the same way, there are no methodologies promoting a ring opening of epoxides using diazocompounds as carbon nucleophiles. (AU)

Scientific publications

(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)

CAIUBY, CLARICE A. D.; FURNIEL, LUCAS G.; BURTOLOSO, ANTONIO C. B.. symmetric transformations from sulfoxonium ylide. CHEMICAL SCIENCE, v. 13, n. 5, DEC 2021. (18/17800-3, 20/07147-0, 20/11955-5, 17/23837-4)

CAIUBY, CLARICE A. D.; VIDAL, LUCAS; BURTOLOSO, ANTONIO C. B.; AISSA, CHRISTOPHE. Cyclic Sulfoxonium Ylides: Synthesis and Chemospecific Reactivity in the Catalytic Alkylation of Indoles. CHEMCATCHEM, v. 15, n. 7, p. 6-pg., 2023-03-08. (20/07147-0, 17/23837-4, 20/11955-5)

CAIUBY, CLARICE A. D.; DE JESUS, MATHEUS P.; BURTOLOSO, ANTONIO C. B.. alpha-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles. Journal of Organic Chemistry, v. 85, n. 11, p. 7433-7445, JUN 5 2020. (09/54040-8, 13/50228-8, 17/23837-4, 17/23329-9)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

CAIUBY, Clarice Alves Dale. Exploring the reactivity of diazocarbonyl compounds and sulfur ylides for the formation of carbon-carbon and carbon-heteroatom bonds. 2023. Doctoral Thesis - Universidade de São Paulo (USP). Instituto de Química de São Carlos (IQSC/BT) São Carlos.