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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Rosset, Isac G. [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 2
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
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 type: 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 type: Regular Research Grants