Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 43, Pages 5889-5904Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800911
Keywords
1,3-Dipolar reactions; Cycloaddition; Asymmetric catalysis; Organocatalysis; Medicinal chemistry
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Funding
- Ministerio de Economia y Competitividad (MINECO) of Spain
- FEDER [CTQ2016-80375-P, CTQ2014-51912-REDC]
- Basque Government (GV/EJ) [IT-324-07]
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The (3+2) cycloaddition between azomethine ylides and alkenes is an efficient, convergent and stereocontrolled method for the synthesis of unnatural pyrrolidine and proline scaffolds. In this review, the application of this reaction to the synthesis of enantiopure organometallic ligands for asymmetric catalysis is presented first. These new EhuPhos ligands can participate in a second generation of 1,3-dipolar reactions that generate an offspring of unnatural proline derivatives that behave as efficient organocatalysts. These densely substituted unnatural l-proline derivatives exhibit distinct features, different to those described for natural l-proline and its derivatives. Finally, several examples of biologically active proline derivatives obtained by means of (3+2) cycloadditions involving azomethine ylides are presented. These applications show the character of privileged structures of these polysubstituted pyrrolidine rings.
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