期刊
PURE AND APPLIED CHEMISTRY
卷 91, 期 4, 页码 575-596出版社
WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2018-0710
关键词
1,3-dipolar cycloadditions; azomethine ylides; carbonyl compounds; Distinguished Women in Chemistry and Chemical Engineering; electrophilic alkene; iminium ions; indolizidines; multicomponent reactions; pyrrolizidines
资金
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43446-P, CTQ2014-51912-REDC]
- Spanish Ministerio de Economia, Industria y Competitividad, Agencia Estatal de Investigacion (AEI)
- Fondo Europeo de Desarrollo Regional (FEDER, EU) [CTQ2016-76782-P, CTQ2016-81797-REDC]
- Generalitat Valenciana [PROMETEOII/2014/017]
- University of Alicante
Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic alpha-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic alpha-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic alpha-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.
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