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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 type:Scholarships in Brazil - Doctorate
Effective date (Start): March 01, 2018
Effective date (End): July 31, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Clarice Alves Dale Caiuby
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

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)