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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.)

Regioselective Functionalization of Ester-, Amide-, Carbonate-, and Carbamate-Substituted 2-Phenyl-2-oxazolines with Mixed Lithium-Magnesium Amides

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Bozzini, Leandro A. [1] ; dos Santos, Thiago [1] ; Murie, Valter E. [1] ; de Mello, Murilo B. M. [1] ; Vessecchi, Ricardo [2] ; Clososki, Giuliano C. [1]
Total Authors: 6
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, Av Do Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14090901 Ribeirao Preto, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 86, n. 1, p. 1204-1215, JAN 1 2021.
Web of Science Citations: 0

We have prepared novel highly functionalized benzene derivatives by regioselective metalation of ester-, amide-, carbamate-, and carbonate-substituted 2-phenyl-2-oxazolines with mixed lithium-magnesium amides followed by reaction with different electrophiles. While a complementary metalation site can be accessed by using different bases, steric and electronic effects promoted by the aromatic ring substituents also play an important role in reaction regioselectivity. Computational calculations of the aromatic hydrogen pK(a) values have helped us to rationalize the metalation preference by the complex-induced proximity effect concept. (AU)

FAPESP's process: 18/14150-8 - Selective aromatic functionalization: Methodological Studies and new applications in the synthesis of BIOATIVE compounds
Grantee:Giuliano Cesar Clososki
Support type: Regular Research Grants
FAPESP's process: 15/21364-6 - Applicantion of Organometallic Reagents in the Directed Functionalization of Quinolines Aimming the Synthesis of Medicinal Interest Compounds
Grantee:Valter Eduardo Murie
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 14/23604-1 - Computational chemistry: a tool to studies of mass spectrometry, reactivity and fragmentation/reaction mechanisms of organic compounds
Grantee:Ricardo Vessecchi Lourenço
Support type: Regular Research Grants