Exploring 5-isoxazolones for the synthesis of beta-aminoacids

• Grant number: 14/15718-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: October 01, 2014
• End date: September 30, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Igor Dias Jurberg
• Grantee: Naylil Malagutti Rodrigues Capreti
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

In this project, we plan to study the conjugate addition of several nucleophiles to alkylidene isoxazolones in a enantioselective fashion. For this purpose, we will primarily investigate a racemic version followed by enantioselective variations of selected processes. The adducts will be submitted to a series of reductive protocols aiming at the establishment of an efficient transformation towards beta-aminoacids derivatives, such as the carboxylic acid, ester or amide. (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)

CAPRETI, NAYLIL M. R.; JURBERG, IGOR D.. Michael Addition of Soft Carbon Nucleophiles to Alkylidene Isoxazol-5-ones: A Divergent Entry to beta-Branched Carbonyl Compounds. ORGANIC LETTERS, v. 17, n. 10, p. 2490-2493, MAY 15 2015. (13/09680-4, 14/15718-7)

BERTUZZI, DIEGO L.; BECHER, TIAGO B.; CAPRETI, NAYLIL M. R.; AMORIM, JULIO; JURBERG, IGOR D.; MEGIATTO, JR., JACKSON D.; ORNELAS, CATIA. General Protocol to Obtain D-Glucosamine from Biomass Residues: Shrimp Shells, Cicada Sloughs and Cockroaches. GLOBAL CHALLENGES, v. 2, n. 11, NOV 2018. (18/02093-0, 15/04929-0, 17/24017-0, 14/15718-7, 13/22160-0)

STIVANIN, MATEUS L.; DUARTE, MARCELO; SARTORI, CAMILA; CAPRETI, NAYLIL M. R.; ANGOLINI, CELIO F. F.; JURBERG, IGOR D.. An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights. Journal of Organic Chemistry, v. 82, n. 19, p. 10319-10330, OCT 6 2017. (15/20809-4, 16/12749-4, 14/15718-7, 15/01331-6)