Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

被引:37
作者
Najera, Carmen [1 ,2 ]
Miguel Sansano, Jose [1 ,2 ,3 ]
机构
[1] Univ Alicante, Dept Quim Organ, Apdo 99, E-03080 Alicante, Spain
[2] Univ Alicante, Ctr Innovac Quim Avanzada ORFEO CINQA, Apdo 99, E-03080 Alicante, Spain
[3] Univ Alicante, Inst Sintesis Organ, Apdo 99, E-03080 Alicante, Spain
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; ONE-POT SYNTHESIS; NONPEPTIDIC THROMBIN INHIBITORS; MEDIATED 3+2 CYCLOADDITION; STRUCTURE-BASED DESIGN; ALPHA-AMINO-ACIDS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SPIROOXINDOLO-PYRROLIDINES; REGIOSELECTIVE-SYNTHESIS; POTENTIAL 1,3-DIPOLES;
D O I
10.1515/pac-2018-0710
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:575 / 596
页数:22
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