| Full text | |
| Author(s): |
Fernandes, Alessandra A. G.
[1]
;
Leonarczyk, Ives A.
[2]
;
Ferreira, Marco A. B.
[2]
;
Dias, Luiz Carlos
[1]
Total Authors: 4
|
| Affiliation: | [1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
[2] Fed Univ Sao, Dept Chem, Ctr Excellence Res Sustainable Chem CERSusChem, BR-13565905 Carlos - Brazil
Total Affiliations: 2
|
| Document type: | Journal article |
| Source: | ORGANIC & BIOMOLECULAR CHEMISTRY; v. 17, n. 12, p. 3167-3180, MAR 28 2019. |
| Web of Science Citations: | 1 |
| Abstract | |
In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of -alkoxy and ,-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the position and the stereoelectronic influence of the oxygen protecting groups at the and positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the -substituent. The synergistic effect between the ,-syn and ,-anti-bisalkoxy stereocenters was elucidated. In the presence of the -alkoxy center, the reaction proceeds through the Goodman-Paton 1,5-stereoinduction model, experiencing a minor influence of the -alkoxy center. (AU) | |
| 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: | 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 |