A stereoselective sequential organocascade and multicomponent approach for the preparation of tetrahydropyridines and chimeric derivatives

Author(s)

Echemendia, Radell ^{[1, 2]} ; da Silva, Gustavo P. ^[2] ; Kawamura, Meire Y. ^[2] ; de la Torre, Alexander F. ^{[3, 2]} ; Correa, Arlene G. ^[2] ; Ferreira, Marco A. B. ^[2] ; Rivera, Daniel G. ^[1] ; Paixao, Marcio W. ^[2]

Affiliation

^[1] Univ Havana, Fac Chem, Ctr Nat Prod Res, Havana 10400 - Cuba

^[2] Fed Univ Sao Carlos UFSCar, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, Rodovia Washington Luis, Km 235, SP-310, BR-13565905 Sao Carlos, SP - Brazil

^[3] Univ Concepcion, Fac Chem Sci, Concepcion - Chile

• Document type: Journal article
• Source: CHEMICAL COMMUNICATIONS; v. 55, n. 3, p. 286-289, JAN 11 2019.
• Web of Science Citations: 4

Abstract

A stereoselective multicomponent approach leading to a novel class of pentasubstituted tetrahydropyridines is described. Variation of the components enabled the incorporation of peptide, sugar and steroid moieties to access chimeric derivatives. DFT calculations provide insights about the unprecedented high diastereoselectivity of the MCR. (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: 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: 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: 15/08541-6 - Nuclear magnetic resonance spectroscopy: beyond molecular structure assignment
• Grantee: Claudio Francisco Tormena
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 16/12622-4 - Asymmetric Counteranion-Directed Organocatalysis: Synthesis of Heterocyclic Systems and Peptides Functionalization
• Grantee: Márcio Weber Paixão
• Support Opportunities: Scholarships abroad - Research