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Asymmetric Aza-Michael addition from unsaturated diazoketones

Grant number: 15/22003-7
Support type:Scholarships in Brazil - Post-Doctorate
Effective date (Start): April 01, 2016
Effective date (End): March 29, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Patrícia Betoni Momo
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
Associated research grant:13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors, AP.TEM
Associated scholarship(s):18/19105-0 - Exploring noncovalent catalysis in enantioselective reactions with diazoketones and Sulfoxonium ylides, BE.EP.PD

Abstract

Pyrrolidine, indolizidine and pyrrolizidine lkaloids are widely studied due to its medicinal properties, for example, antifungal, antibacterial, antiviral, antitumor activity and others. In view of this, methodologies enabling access to these compounds in a few steps and efficiently are big draws for organic chemistry. In this project we propose the study of asymmetric aza-Michael reactions from ±,²-unsaturated diazoketones, aiming the formation of chiral ²-amino diazoketones. The diazoketones will be prepared from Horner-Wadsworth-Emmons (HWE) olefination reactions between diazophosphonates and aldehydes. In sequence, methodological studies will be conducted for the asymmetric aza-Michael reaction employing chiral amines and asymmetric catalysts. Adducts will be then subjected to intramolecular N-H insertion reactions. Hydroxylated alkaloids from the prepared pyrrolidinones will be submited to biological studies. Another part of the project will be dedicated to the synthesis of pyrrolizidine and indolizidine skeletons from diazoketones.

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)
ANTONIO C.B. BURTOLOSO; PATRÍCIA B. MOMO; GRAZIELE L. NOVAIS. Traditional and New methods for the Preparation of Diazocarbonyl Compounds. Anais da Academia Brasileira de Ciências, v. 90, n. 1, p. -, 2018.
BURTOLOSO, ANTONIO C. B.; MOMO, PATRICIA B.; NOVAIS, GRAZIELE L. Traditional and New methods for the Preparation of Diazocarbonyl Compounds. Anais da Academia Brasileira de Ciências, v. 90, n. 1, 1, p. 859-893, 2018. Web of Science Citations: 5.
DIAS, RAFAEL M. P.; MOMO, PATRICIA B.; BURTOLOSO, ANTONIO C. B. One-step syntheses of substituted 2-pyrrolidinones and 3-pyrrolidinones from alpha,beta-unsaturated diazoketones and amines. Application in the synthesis of barmumycin. Tetrahedron, v. 73, n. 26, p. 3720-3729, JUN 29 2017. Web of Science Citations: 7.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.