| Full text | |
| 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 |