Organocatalytic insertion reactions for drug discovery

• Grant number: 13/50312-9
• Support Opportunities: Regular Research Grants
• Start date: October 01, 2013
• End date: September 30, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: Ohio State University
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Antonio Carlos Bender Burtoloso
• Principal researcher abroad: Anita Elaine Mattson
• Institution abroad: Ohio State University, Columbus, United States
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Associated research grant: 12/04685-5 - New synthetic methodologies for the construction of pyrrolidine, piperidine and indolizidine systems, AP.R

Abstract

A comprehensive research program with the long-term goal of discovering sustainable methods for drug target synthesis is proposed. Specifically, organocatalytic insertion reactions will be investigated. En route to realizing this goal, the objectives of this proposed research agenda include (i) exploring urea and phosphoric acid derivatives as catalysts for N-H and O-H insertion reactions of diazo compounds and (ii) applying innovative organocatalytic insertion reactions toward the syntheses of active pharmaceutical ingredients. The specific aims included in this proposed research plan are: 1) Study the activation of diazo compounds for insertion reactions with chiral urea catalysis (Mattson Laboratories - OSU), 2) Investigate the activation of diazo compounds for insertion reactions with chiral phosphoric acid-derived catalysis (Burtoloso Laboratories - USP) and 3) Apply new methods organocatalytic insertion methods toward the enantioselective syntheses of durg targets, including bupropion, duloxetine and fluoxetine (Burtoloso and Mattson Laboratories). (AU)

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)

BERNARDIM, BARBARA; COUCH, ERICA D.; HARDMAN-BALDWIN, ANDREA M.; BURTOLOSO, ANTONIO C. B.; MATTSON, ANITA E.. Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds. SYNTHESIS-STUTTGART, v. 48, n. 5, p. 677-686, MAR 2016. (13/50312-9, 13/18009-4, 12/22274-2, 13/25504-1)