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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.)

Organocatalyzed Asymmetric Vinylogous Addition of Oxazole-2(3H)-thiones to alpha,beta-Unsaturated Ketones: An Additive-Free Approach for Diversification of Heterocyclic Scaffold

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Author(s):
Silva, Sandrina [1] ; Matsuo, Bianca T. [1] ; da Silva, Rodrigo C. [1] ; Pozzi, Lucas V. [1] ; Correa, Arlene G. [1] ; Rollin, Patrick [2, 3] ; Zukerman-Schpector, Julio [1] ; Ferreira, Marco A. B. [1] ; Paixao, Marcio W. [1]
Total Authors: 9
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Orleans, F-45067 Orleans - France
[3] CNRS, ICOA, UMR 7311, BP 6759, F-45067 Orleans - France
Total Affiliations: 3
Document type: Journal article
Source: Journal of Organic Chemistry; v. 83, n. 4, p. 1701-1716, FEB 16 2018.
Web of Science Citations: 2
Abstract

A straightforward organocatalyzed asymmetric addition of oxazole-2(3H)-thiones to alpha,beta-unsaturated ketones is described. This additive-free Michael reaction in the presence of chiral cinchonine-derived primary amines as catalysts has proven to be highly effective for a wide range of cyclic and acyclic enones, leading to the Michael adducts in very good yields and excellent enantioselectivities. The absolute configuration (R) of compound 5j was unambiguously assigned by X-ray diffraction analysis. Furthermore, experimental and theoretical studies were performed and a mechanism is presented and discussed for this novel reaction. (AU)

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: 12/04986-5 - Asymmetric Organocatalysis: Development of New Methodologies and Application in Total Synthesis
Grantee:Sandrina Isabel Ribeiro Martins da Silva
Support Opportunities: Scholarships in Brazil - Post-Doctoral
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: 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