Article ; Online: Augmentation of Enantioselectivity by Spatial Tuning of Aminocatalyst: Synthesis of 2-Alkyl/aryl-3-nitro-2
The Journal of organic chemistry
2020 Volume 85, Issue 7, Page(s) 4627–4636
Abstract: The asymmetric oxa-Michael addition of salicylaldehyde to conjugated nitroalkenes often suffers from poor reactivity and selectivity and a long reaction time. Because of the formation of an iminium ion with aminocatalyst, the nucleophilicity of the ... ...
Abstract | The asymmetric oxa-Michael addition of salicylaldehyde to conjugated nitroalkenes often suffers from poor reactivity and selectivity and a long reaction time. Because of the formation of an iminium ion with aminocatalyst, the nucleophilicity of the phenolic hydroxy group in salicylaldehyde reduces further to make the oxa-Michael reaction reversible. Here, we report a structurally simple and easily accessible l-proline derived aminocatalyst, phenyl l-prolinamide, for asymmetric tandem oxa-Michael-Henry reaction of salicylaldehyde with conjugated nitroalkene to give 2-alkyl/aryl-3-nitro-2 |
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Language | English |
Publishing date | 2020-03-13 |
Publishing country | United States |
Document type | Journal Article |
ZDB-ID | 123490-0 |
ISSN | 1520-6904 ; 0022-3263 |
ISSN (online) | 1520-6904 |
ISSN | 0022-3263 |
DOI | 10.1021/acs.joc.9b03366 |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
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