| Full text | |
| 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]
Total Authors: 9
|
| 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
Total Affiliations: 3
|
| 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 - Applied Research Centers 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 |