Thia-Michael additions and insertion reactions in a,b-unsaturated sulfur ylides

• Grant number: 18/02920-3
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: May 01, 2018
• End date: December 31, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Eduardo Falcão Mizobuchi
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

Sulfur compounds are present in a wide array of natural and non natural products with relevant biological activity. Thus, these compounds have great importance in the medicinal, biochemical and synthetic areas. Tetrahydrothiophenes are sulfur heterocycles composed by a five atoms ring and are present in important bioactive compounds such as biotine. This class of compounds also presents great importance in organic synthesis acting as building blocks or as catalysts in some type of reactions. This project proposes a new metodology fot the synthesis of tetrahydrothiophenes using the chemistry of sulfur ylides. The sulfur ylides will be prepared by the reaction between a,b-unsaturated carboxylic acid derivatives and dimethylsulfoxonium methylide. Then, studies of thia-Michael addition will be performed. The obtained adducts will go under deprotection reactions, forming S-H groups for posterior intramolecular insertion raction, aiming to obtain the tetrahydrothiophenes.

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)

MOMO, PATRICIA B.; MIZOBUCHI, EDUARDO F.; ECHEMENDIA, RADELL; BADDELEY, ISABEL; GRAYSON, MATTHEW N.; BURTOLOSO, ANTONIO C. B.. Organocatalytic Enantioselective Sulfa-Michael Additions to alpha,beta-Unsaturated Diazoketones. Journal of Organic Chemistry, v. 87, n. 5, p. 9-pg., 2022-03-04. (19/12300-5, 20/07147-0, 17/23329-9, 18/02920-3, 15/22003-7)