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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.)

Multicomponent Combinatorial Development and Conformational Analysis of Prolyl Peptide-Peptoid Hybrid Catalysts: Application in the Direct Asymmetric Michael Addition

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Author(s):
de la Torre, Alexander F. [1] ; Rivera, Daniel G. [1, 2] ; Ferreira, Marco A. B. [1] ; Correa, Arlene G. [1] ; Paixao, Marcio W. [1]
Total Authors: 5
Affiliation:
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Havana, Fac Chem, Ctr Nat Prod Study, Havana 10400 - Cuba
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 78, n. 20, p. 10221-10232, OCT 18 2013.
Web of Science Citations: 19
Abstract

A solution-phase combinatorial approach based on the Ugi four-component reaction was implemented for the development of new prolyl peptide-peptoid hybrid catalysts. Three different elements of diversity were varied during the creation of the set of catalysts: the amine, oxo, and isocyano components. The multicomponent nature of this process enabled the straightforward generation of a series of peptide-peptoid hybrids having the generic sequence Pro-N-R-1-Xaa-NHR3, with Xaa being either Gly (R-2 = H) or Aib (R-2 = gem-Me) and R-1 and R-3 either alkyl or amino acid substituents. The catalytic behavior of the peptide-peptoid hybrids was assessed in the asymmetric conjugate addition of aldehydes to nitroolefins, where most of the catalysts showed great efficacy and rendered the Michael adducts with good to excellent enantio- and diastereoselectivity. A molecular modeling study was performed for two distinct catalysts aiming to understand their conformational features. The conformational analysis provided important information for understanding the remarkable stereocontrol achieved during the organocatalytic transformation. (AU)

FAPESP's process: 13/02311-3 - New approaches in asymmetric synthesis of tetrahydrofuran and tetrahydropyran-derivatives with potential application in the preparation of bioactive molecules
Grantee:Marco Antonio Barbosa Ferreira
Support Opportunities: Regular Research Grants
FAPESP's process: 09/07281-0 - Asymmetric organocatalysis: design of new organocatalysts and development of new methodologies
Grantee:Márcio Weber Paixão
Support Opportunities: Research Grants - Young Investigators Grants