Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes
A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic st...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00223263_v66_n4_p1387_Nudelman |
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todo:paper_00223263_v66_n4_p1387_Nudelman2023-10-03T14:31:24Z Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes Nudelman, N.S. García, G.V. aldehyde derivative chalcone derivative cinnamaldehyde dihydrochalcone lithium derivative phenyllithium unclassified drug alkylation article chemical structure nuclear magnetic resonance spectroscopy reaction analysis synthesis A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic steps of this new reaction. Extended studies revealed that β-alkyl-substituted α,β-unsaturated aldehydes and aliphatic lithium reagents did not afford good yields of the tandem reaction products, while aromatic lithium reagents gave good results. The aggregation features of the aryllithium reagents and the extended charged delocalization effects are considered to promote β-selectivity. This approach provides a convenient route for the synthesis of a wide variety of β-alkyl-substituted dihydrochalcones. Fil:García, G.V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00223263_v66_n4_p1387_Nudelman |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
aldehyde derivative chalcone derivative cinnamaldehyde dihydrochalcone lithium derivative phenyllithium unclassified drug alkylation article chemical structure nuclear magnetic resonance spectroscopy reaction analysis synthesis |
| spellingShingle |
aldehyde derivative chalcone derivative cinnamaldehyde dihydrochalcone lithium derivative phenyllithium unclassified drug alkylation article chemical structure nuclear magnetic resonance spectroscopy reaction analysis synthesis Nudelman, N.S. García, G.V. Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| topic_facet |
aldehyde derivative chalcone derivative cinnamaldehyde dihydrochalcone lithium derivative phenyllithium unclassified drug alkylation article chemical structure nuclear magnetic resonance spectroscopy reaction analysis synthesis |
| description |
A tandem reaction between (E)-cinnamaldehyde, 1a, and phenyllithium affording β-substituted dihydrochalcones was recently reported. NMR spectroscopic studies on the reaction mixture, as well as isotopic exchange reactions and trapping of two intermediates, provide clues on the several mechanistic steps of this new reaction. Extended studies revealed that β-alkyl-substituted α,β-unsaturated aldehydes and aliphatic lithium reagents did not afford good yields of the tandem reaction products, while aromatic lithium reagents gave good results. The aggregation features of the aryllithium reagents and the extended charged delocalization effects are considered to promote β-selectivity. This approach provides a convenient route for the synthesis of a wide variety of β-alkyl-substituted dihydrochalcones. |
| format |
JOUR |
| author |
Nudelman, N.S. García, G.V. |
| author_facet |
Nudelman, N.S. García, G.V. |
| author_sort |
Nudelman, N.S. |
| title |
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| title_short |
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| title_full |
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| title_fullStr |
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| title_full_unstemmed |
Tandem addition β-lithiation - Alkylation sequence on α,β-unsaturated aldehydes |
| title_sort |
tandem addition β-lithiation - alkylation sequence on α,β-unsaturated aldehydes |
| url |
http://hdl.handle.net/20.500.12110/paper_00223263_v66_n4_p1387_Nudelman |
| work_keys_str_mv |
AT nudelmanns tandemadditionblithiationalkylationsequenceonabunsaturatedaldehydes AT garciagv tandemadditionblithiationalkylationsequenceonabunsaturatedaldehydes |
| _version_ |
1807322274220474368 |