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Expanding the substrate scope of Ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids.

ABSTRACT: Various symmetrical and unsymmetrical ketones were successfully coupled with secondary amino acids in the course of Ugi five-center, four-component reaction (U-5C-4CR), thus expanding the molecular diversity possible to be achieved by the reaction. The chemical yields depended on the degree of hindrance of the components employed and were satisfactory in view of possible steric interactions in the U-5C-4CR zwitterionic intermediate. The sense of diastereoinduction for reactions employing unsymmetrical ketones was examined by converting the resulting Ugi adducts into the corresponding rigid 2,6-diketopiperazine derivatives.

SUBMITTER: Dawidowski M

PROVIDER: S-EPMC3906574 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Expanding the substrate scope of Ugi five-center, four-component reaction U-5C-4CR): ketones as coupling partners for secondary amino acids.

Dawidowski Maciej M Sobczak Sławomir S Wilczek Marcin M Kulesza Artur A Turło Jadwiga J

Molecular diversity 20131024 1

Various symmetrical and unsymmetrical ketones were successfully coupled with secondary amino acids in the course of Ugi five-center, four-component reaction (U-5C-4CR), thus expanding the molecular diversity possible to be achieved by the reaction. The chemical yields depended on the degree of hindrance of the components employed and were satisfactory in view of possible steric interactions in the U-5C-4CR zwitterionic intermediate. The sense of diastereoinduction for reactions employing unsymme ...[more]

PMID: 24154732

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