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The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2568876/ https://www.ncbi.nlm.nih.gov/pubmed/18941617 http://dx.doi.org/10.3762/bjoc.4.32 |
Sumario: | The impact of a remote aromatic nucleus on the stereochemical outcome of the conjugate addition of α-sulfonylallylic carbanions to an α,β-unsaturated ester was investigated. α-Regioselectivity coupled with anti-diastereoselectivity is accompanied by a prominent preference for relative configuration 3 over 4. The 9-anthryl moiety has shown itself greatly superior over all other groups in this bias. A lithium ion–aromatic π interaction has been postulated as decisive for the remote transmission of chirality. |
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