Abstract
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.
| Original language | English |
|---|---|
| Article number | 32 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume | 4 |
| DOIs | |
| State | Published - 23 Sep 2008 |
Keywords
- Cation-π interaction
- Conjugate addition
- Diastereoselectivity
- Regioselectivity
- Remote chiral induction