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ENANTIOSELECTIVE ALPHA-HETEROFUNCTIONALIZATION OF CARBONYL COMPOUNDS USING SULFOXONIUM YLIDES

Grant number: 20/07147-0
Support type:Regular Research Grants
Duration: November 01, 2020 - October 31, 2022
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Antonio Carlos Bender Burtoloso
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

Alpha-Heterofunctionalized carbonyl compounds have a wide versatility as synthetic building blocks, due to a variety of transformations that these can participate. However, there are a limited number of asymmetric methodologies to prepare this class of compounds. Therefore, the development of such methodologies is of great importance in the area of organic synthesis. Combining this need with the synthetic potential of sulfur ylides, this project aims to develop new methodologies using these ylides for enantioselective alpha-heterofunctionalization of carbonyl compounds employing metals and organocatalysts. To do so, asymmetric N-H and O-H insertion reactions with acylated sulfur ylides will be evaluated. This strategy would allow the access to alpha-aminocarbonyl, alpha-hydroxy esthers and alpha-carbonyl ethers. There are no reports in the literature for this transformation in an asymmetric fashion. The asymmetric synthesis of alpha-halogenated and alpha-sulfenyl carbonyl compounds will also be evaluated by means of S-H insertion, alkylation/halogenation and dehalogenation reactions. (AU)