The alpha-alkylation of carbonyl sulfoxonium ylides: studies and applications in the synthesis of new sulfur heterocycles

Author(s)

de Jesus, Matheus P. ; Echemendia, Radell ; Burtoloso, Antonio C. B.

• Document type: Journal article
• Source: ORGANIC CHEMISTRY FRONTIERS; v. 10, n. 14, p. 8-pg., 2023-06-09.

Abstract

The challenging direct alpha-alkylation of sulfoxonium ylides is demonstrated after a deep study with several electrophiles. Twenty-five alkylated ester sulfoxonium ylides could be prepared in 12-67% isolated yields, employing Michael acceptors as electrophiles. Interestingly, no product arising from the classical cyclopropanation reaction, commonly observed for the reaction between sulfur ylides and Michael acceptors, was observed. To demonstrate the applicability of these unprecedented and more decorated sulfoxonium ylides, new and medicinal-chemistry important sulfur heterocycles, such as 2-mercaptobenzothiazoles, 1,4-benzothiazin-3-ones, and coumarin derivatives, were prepared. (AU)

• FAPESP's process: 19/12300-5 - Synthesis of butenolides and butyrolactams from sulfur ylides and diazocompounds
• Grantee: Radell Echemendía Pérez
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 20/07147-0 - Enantioselective alpha-heterofunctionalization of carbonyl compounds using sulfoxonium ylides
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants
• FAPESP's process: 20/07143-5 - Studies aiming the preparation of pro-chiral ²-ceto sulfoxônios -ketosulfoxonium ylides and their applications in the synthesis of isoquinoline derivatives
• Grantee: Matheus Pereira de Jesus
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)