Exploring the formation of new C-C bonds through the reaction of sulfur ylides with epoxides

• Grant number: 23/11525-9
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: October 01, 2023
• End date: July 31, 2024
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Aislan Leme da Silva
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

Sulfur ylides consist of a chemical class that is currently establishing itself as versatile substrates in organic synthesis. Its structural characteristics guarantee an ambiphilic character, allowing sulfur ylides to participate in reactions with different electrophiles and nucleophiles.Although the ²-keto sulfoxonium ylides have a wide range of synthetic applications, one of the less explored applications is their use as nucleophiles in the face of epoxide opening reactions. Epoxides have great synthetic utility since they have a very versatile reactivity, with emphasis on opening reactions using nucleophiles. These reactions lead to the formation of 1,2-disubstituted products and also of oxetanes, as described in the work of Okuma et al. in 1983.As there are still no reports in the literature on the use of functionalized ylides, such as ²-ketosulfoxonium, in the synthesis of oxetanes from the opening of epoxides, this project proposes the study of this type of reaction, in order to obtain oxetanes of greater structural complexity. For this, a library of epoxides with different patterns of reactivity will be synthesized, based on methods described in the literature. The first method consists of the epoxidation of alkenes using meta-chloroperbenzoic acid (mCPBA). The second method to be used consists of the Corey and Chaykovsky epoxidation reaction, which generates the epoxide from carbonyl compounds. In a second moment, the opening reaction of these epoxides will be tested using the ²-keto sulfoxonium ylides as nucleophiles.