Exploring noncovalent catalysis in enantioselective reactions with diazoketones and sulfoxonium ylides

• Grant number: 18/19105-0
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• Start date: December 01, 2018
• End date: November 29, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Antonio Carlos Bender Burtoloso
• Grantee: Patrícia Betoni Momo
• Supervisor: Anita E. Mattson
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil
• Institution abroad: Worcester Polytechnic Institute (WPI), United States
• Associated to the scholarship: 15/22003-7 - Asymmetric Aza-Michael Addition from unsaturated diazoketones., BP.PD

Abstract

Our research group have been exploring the chemistry of a,b-unsaturated diazoketones and b-ketosulfoxonium ylides and using these compounds in several relevant chemical transformations. Currently, we are studying enantioselective reactions employing a,b-unsaturated diazoketones, aryl and alkyl diazoketones and b-ketosulfoxonium ylides. In this project, enantioselective reactions will be done exploring the use of hydrogen-bonding donor catalysts via two different activation modes: direct or anion-binding. To Michael addition reactions, we will use unsaturated diazoketones and sulfoxonium ylides as acceptor and amines and indoles as donors. Moreover, we also intend to perform enantioselective dihalogenation and S-H insertion reactions from b-sulfoxonium ylides employing the same organocatalytic strategies for Michael addition. (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)

MOMO, PATRICIA B.; LEVEILLE, ALEXANDRIA N.; FARRAR, ELLIOT H. E.; GRAYSON, MATTHEW N.; MATTSON, ANITA E.; BURTOLOSO, ANTONIO C. B.. Enantioselective S-H Insertion Reactions of alpha-Carbonyl Sulfoxonium Ylides. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 59, n. 36, MAY 2020. (18/19105-0, 13/18009-4, 17/23329-9)