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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.)

Employing Small Polyfunctionalized Molecules for a Diastereoselective Synthesis of Highly Substituted Indolines

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Author(s):
Fernandes, Fabio de Souza [1] ; Cormanich, Rodrigo A. [1] ; Zeoly, Lucas A. [1] ; Formiga, Andre Luiz B. [2] ; Coelho, Fernando [1]
Total Authors: 5
Affiliation:
[1] Univ Estadual Campinas, Dept Organ Chem, Inst Chem, Campinas, SP - Brazil
[2] Univ Estadual Campinas, Dept Inorgan Chem, Inst Chem, Rua Josue de Castro S-N, POB 6154, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2018, n. 24, p. 3211-3223, JUN 29 2018.
Web of Science Citations: 4
Abstract

An efficient approach has been developed for the diastereoselective synthesis of 1,2,3-trisubstituted indolines. The reaction sequence includes the highly diastereoselective reductive amination of 2-oxo-1,3-propanediols, which are prepared by postfunctionalization of Morita-Baylis-Hillman (MBH) adducts, to give substituted 2-amino-1,3-propanediols with an anti relative configuration. A subsequent intramolecular palladium-catalyzed Buchwald coupling reaction provided the 1,2,3-trisubstituted indolines in 47-82% yield. The preference for the anti diastereomer was investigated by Gibbs free energy diagrams and applying theoretical calculations at the M06-2X/6-31+G{*}{*} level. (AU)

FAPESP's process: 17/02364-0 - Mechanistic investigations of the biginelli reaction using experimental and theoretical approaches
Grantee:Rodrigo Antonio Cormanich
Support Opportunities: Scholarships abroad - Research
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC