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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.)

Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction

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Fernandes, Vitor A. [1] ; Lima, Rafaely N. [1] ; Broterson, Yoisel B. [1] ; Kawamura, Meire Y. [1] ; Echemendia, Radell [1, 2] ; de la Torre, Alexander F. [3] ; Ferreira, Marco A. B. [1] ; Rivera, Daniel G. [2] ; Paixao, Marcio W. [1]
Total Authors: 9
[1] Univ Fed Sao Carlos, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Havana, Fac Chem, Havana - Cuba
[3] Univ Concepcion, Fac Ciencias Quim, Dept Quim Organ, Concepcion - Chile
Total Affiliations: 3
Document type: Journal article
Source: CHEMICAL SCIENCE; v. 12, n. 48 SEP 2021.
Web of Science Citations: 0

An efficient strategy combining the stereocontrol of organocatalysis with the diversity-generating character of multicomponent reactions is described to produce structurally unique, tetrasubstituted cyclopentenyl frameworks. An asymmetric Michael addition-hemiacetalization between alpha-cyanoketones and alpha,beta-unsaturated aliphatic aldehydes was performed for constructing cyclic hemiacetals, which were next employed as chiral bifunctional substrates in a new diastereoselective intramolecular isocyanide-based multicomponent reaction. This approach furnished a diversity of structurally complex compounds - including peptidomimetics and natural product hybrids in high stereoselectivity (up to >99% ee and up to >99 : 1 dr) and in moderate to high yields. (AU)

FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
Grantee:Ricardo Samuel Schwab
Support Opportunities: Regular Research Grants
FAPESP's process: 17/01754-0 - Experimental and theoretical studies on cycloaddition (3 + 2) reactions of azides to nitro-olefins
Grantee:Meire Yasuko Kawamura
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program
FAPESP's process: 20/01255-6 - Application of statistical tools in catalysis for understanding and predicting organic reactions
Grantee:Marco Antonio Barbosa Ferreira
Support Opportunities: Regular Research Grants
FAPESP's process: 20/10246-0 - Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments
Grantee:Claudio Francisco Tormena
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 19/01973-9 - Exploration of the Asymmetric Induction in Ugi Variations Aiming the Stereoselective Synthesis and Functionalizationof N-Heterocycles
Grantee:Vitor Alcantara Fernandes da Silva
Support Opportunities: Scholarships in Brazil - Doctorate