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...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2008-09-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.4.32 |
| id |
doaj-4b3ec2154cce45d2876aad829526d004 |
|---|---|
| record_format |
Article |
| spelling |
doaj-4b3ec2154cce45d2876aad829526d0042021-02-02T08:18:05ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972008-09-01413210.3762/bjoc.4.321860-5397-4-32The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonateShlomo Levinger0Ranjeet Nair1Alfred Hassner2Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, IsraelDepartment of Chemistry, Bar-Ilan University, Ramat-Gan 52900, IsraelDepartment of Chemistry, Bar-Ilan University, Ramat-Gan 52900, IsraelThe 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.https://doi.org/10.3762/bjoc.4.32cation–π interactionconjugate additiondiastereoselectivityregioselectivityremote chiral induction |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Shlomo Levinger Ranjeet Nair Alfred Hassner |
| spellingShingle |
Shlomo Levinger Ranjeet Nair Alfred Hassner The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate Beilstein Journal of Organic Chemistry cation–π interaction conjugate addition diastereoselectivity regioselectivity remote chiral induction |
| author_facet |
Shlomo Levinger Ranjeet Nair Alfred Hassner |
| author_sort |
Shlomo Levinger |
| title |
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_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_sort |
role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2008-09-01 |
| 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. |
| topic |
cation–π interaction conjugate addition diastereoselectivity regioselectivity remote chiral induction |
| url |
https://doi.org/10.3762/bjoc.4.32 |
| work_keys_str_mv |
AT shlomolevinger theroleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate AT ranjeetnair theroleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate AT alfredhassner theroleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate AT shlomolevinger roleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate AT ranjeetnair roleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate AT alfredhassner roleofanaromaticgroupinremotechiralinductionduringconjugateadditionofasulfonylallyliccarbanionstoethylcrotonate |
| _version_ |
1724297463218569216 |