Preparation of Z-alpha,beta-Unsaturated Diazoketones from Aldehydes. Application in the Construction of Substituted Dihydropyridin-3-ones

Author(s)

Rosset, Isac G. ^[1] ; Burtoloso, Antonio C. B. ^[1]

Affiliation

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

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 78, n. 18, p. 9464-9470, SEP 20 2013.
• Web of Science Citations: 11

Abstract

The stereoselective preparation of alpha,beta-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N-H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the utility of these unsaturated diazoketones for the rapid construction of piperidines. (AU)

• FAPESP's process: 10/18801-1 - DIVERGENT SYNTHESIS OF PYRROLIDINE ALKALOIDS FROM ALFA,BETAUNSATURATED DIAZOKETONES AS BIFUNCTIONAL REAGENTS. APPLICATION IN THE TOTAL SYNTHESIS OF (±)-PREUSSIN
• Grantee: Isac George Rosset
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/04685-5 - New synthetic methodologies for the construction of pyrrolidine, piperidine and indolizidine systems
• Grantee: Antonio Carlos Bender Burtoloso
• Support Opportunities: Regular Research Grants