Enantioselective S-H Insertion Reactions of alpha-Carbonyl Sulfoxonium Ylides

Author(s)

Momo, Patricia B. ^[1] ; Leveille, Alexandria N. ^[2] ; Farrar, Elliot H. E. ^[3] ; Grayson, Matthew N. ^[3] ; Mattson, Anita E. ^[2] ; Burtoloso, Antonio C. B. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Chem Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[2] Worcester Polytech Inst, Dept Chem & Biochem, 100 Inst Rd, Worcester, MA 01609 - USA

^[3] Univ Bath, Dept Chem, Claverton Down, Bath BA2 7AY, Avon - England

• Document type: Journal article
• Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 59, n. 36 MAY 2020.
• Web of Science Citations: 1

Abstract

The first example of enantioselective S-H insertion reactions of sulfoxonium ylides is reported. Under the influence of thiourea catalysis, excellent levels of enantiocontrol (up to 95 % ee) and yields (up to 97 %) are achieved for 31 examples in S-H insertion reactions of aryl thiols and alpha-carbonyl sulfoxonium ylides. (AU)

• FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
• Grantee: Carlos Alberto Montanari
• Support type: Research Projects - Thematic Grants
• FAPESP's process: 17/23329-9 - Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass
• Grantee: Antonio Carlos Bender Burtoloso
• Support type: Regular Research Grants
• FAPESP's process: 18/19105-0 - Exploring noncovalent catalysis in enantioselective reactions with Diazoketones and Sulfoxonium Ylides.
• Grantee: Patrícia Betoni Momo
• Support type: Scholarships abroad - Research Internship - Post-doctor