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

Author(s)

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]

Affiliation

^[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

• Document type: Journal article
• Source: CHEMICAL SCIENCE; v. 12, n. 48 SEP 2021.
• Web of Science Citations: 0

Abstract

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