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...

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Detalles Bibliográficos
Autores principales: Levinger, Shlomo, Nair, Ranjeet, Hassner, Alfred
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
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
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author Levinger, Shlomo
Nair, Ranjeet
Hassner, Alfred
author_facet Levinger, Shlomo
Nair, Ranjeet
Hassner, Alfred
author_sort Levinger, Shlomo
collection PubMed
description 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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spelling pubmed-25688762008-10-20 The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate Levinger, Shlomo Nair, Ranjeet Hassner, Alfred Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2008-09-23 /pmc/articles/PMC2568876/ /pubmed/18941617 http://dx.doi.org/10.3762/bjoc.4.32 Text en Copyright © 2008, Levinger et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Levinger, Shlomo
Nair, Ranjeet
Hassner, Alfred
The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title_full The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title_fullStr The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title_full_unstemmed The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title_short The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
title_sort role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
topic Full Research Paper
url 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
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