Exploring the formation of new C-C bonds through reaction of sulfur ylides with epoxides and electrophilic species from alkenes

• Grant number: 22/00496-5
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: July 01, 2022
• Status: Discontinued
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Viktor Saraiva Câmara
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated scholarship(s): 24/07727-8 - Exploring the strain-release reaction of bicyclo[1.1.0]butanes and [1.1.1]propellanes with sulfur ylides, BE.EP.PD

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 formation of new C-C bonds using sulfur ylides as nucleophile in the epoxide ring-opening reaction and addition reaction in electrophilic species from alkenes, allowing access to functionalized oxetanes, alpha-functionalized ketones and more complex sulfur ylides. In a first moment, these transformations will be performed in a non-asymmetric mode and, later extended to an asymmetric version. Currently, there are no reports in the literature which successfully uses functionalized sulfur ylides in the opening of epoxides to obtain enantiomerically enriched oxetanos. Also, there are no reports of the use of sulfur ylides in addition reaction to electrophilic species from alkenes. (AU)