Enantioselective synthesis of spirolactones via intramolecular carbonylative Heck-Matsuda reactions with in situ formation of the aryldiazonium salts

• Grant number: 22/07887-0
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate (Direct)
• Start date: November 30, 2022
• End date: November 29, 2023
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Carlos Roque Duarte Correia
• Grantee: Tomaz Henrique Duarte Chorro
• Supervisor: Troels Skrydstrup
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: Aarhus University, Denmark
• Associated to the scholarship: 21/14298-8 - Enantioselective desymmetrization via Heck-Matsuda reactions: development of new methodologies and applications, BP.DD

Abstract

The Heck reactions are very efficient processes for the formation of C-C bonds. Our research group has been working with excellence on the development of Heck Matsuda reactions, a version of the traditional Heck employing arenediazonium salts. Recent important results have shown the possibility of carrying out the one-pot enantioselective Heck Matsuda reaction directly from anilines, without the need for previous synthesis of diazonium salts and this purification. The method developed means a more sustainable process, brought operational simplicity, considerable gains in yields, and the possibility of using aryl diazonium salts that are difficult to prepare or which are potentially explosive. However, the development of the carbonylative version of this reaction remains an enormous synthetic challenge. In this project, we planned to synthesize spirolactones scaffolds from the one-pot Heck Matsuda carbonylative reaction in an enantioselective manner. During the development of this project, several sources of carbon monoxide will be evaluated, taking advantage of the expertise of Professor Troels in the development of CO-Releasing Molecules. (AU)

Scientific publications

(The scientific publications listed on this page originate from the Web of Science or SciELO databases. Their authors have cited FAPESP grant or fellowship project numbers awarded to Principal Investigators or Fellowship Recipients, whether or not they are among the authors. This information is collected automatically and retrieved directly from those bibliometric databases.)

CHORRO, TOMAZ HENRIQUE DUARTE; KAUSSLER, CLEMENS; KOLODIAZHNAIA, JULIA V.; JENSEN, FRANK; SKRYDSTRUP, TROELS; CORREIA, CARLOS ROQUE D.. Tandem synthesis of enantioenriched spirolactones via one-pot Heck-Matsuda reactions directly from nitroarenes. ORGANIC CHEMISTRY FRONTIERS, v. 12, n. 4, p. 9-pg., 2024-12-17. (13/07600-3, 14/25770-6, 21/14298-8, 23/00383-9, 22/07887-0)