Visible-Light-Mediated Strategies to Assemble Alkyl 2-Carboxylate-2,3,3-Trisubstituted beta-Lactams and 5-Alkoxy-2,2,4-Trisubstituted Furan-3(2H)-ones Using Aryldiazoacetates and Aryldiazoketones

Author(s)

Munaretto, Laieli S. ^[1] ; dos Santos, Caio Y. ^[1] ; Gallo, Rafael D. C. ^[1] ; Okada Jr, Celso Y. ; Deflon, Victor M. ^[2] ; Jurberg, Igor D. ^[3]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-13083862 Campinas, SP - Brazil

^[2] Univ Sao Paulo, Inst Chem Sao Carlos, BR-13566590 Sao Carlos, SP - Brazil

^[3] Okada Jr, Jr., Celso Y., Univ Estadual Campinas, Inst Chem, BR-13083862 Campinas, SP - Brazil

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 23, n. 23, p. 9292-9296, DEC 3 2021.
• Web of Science Citations: 0

Abstract

Two new visible-light-mediated strategies are described starting from aryldiazoacetates. The first approach describes their reaction with azides to afford the corresponding imines, and then reaction with aryldiazoketones produces alkyl 2-carboxylate-2,3,3-trisubstituted beta-lactams. The second approach describes the reaction with sulfoxides to afford the corresponding sulfoxonium ylides, followed by reaction with aryldiazoketones to produce S-alkoxy-2,2,4-trisubstituted furan-3(2H)-ones. These protocols take advantage of the photolysis of aryldiazoacetates and the photochemically promoted Wolff rearrangement of aryldiazoketones. (AU)

• FAPESP's process: 19/01235-8 - Photochemistry with visible light using donor-acceptor diazocompounds
• Grantee: Igor Dias Jurberg
• Support Opportunities: Regular Research Grants
• FAPESP's process: 20/00144-6 - Structural proteomics: design, synthesis and application of new generation crosslinking agents
• Grantee: Rafael Douglas Clemente Gallo
• Support Opportunities: Scholarships in Brazil - Post-Doctoral