The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate
2008
The Role of Aromatic Groups in Chiral Induction
publication
Evidence: high
Author Information
Author(s): Levinger Shlomo, Nair Ranjeet, Hassner Alfred
Primary Institution: Bar-Ilan University
Hypothesis
The study investigates how the presence of different aromatic groups affects chiral induction during conjugate addition reactions.
Conclusion
The 9-anthryl group leads to complete transmission of chirality in the conjugate addition of lithiated α-sulfonylallylic carbanions.
Supporting Evidence
- The study found that the 9-anthryl moiety showed superior chiral induction compared to other groups.
- Complete chiral induction was achieved with the 9-anthryl derivative in the conjugate addition reaction.
- Electron-donating aromatic groups resulted in better yields in the reactions.
Takeaway
This study shows that adding certain aromatic groups can help make new molecules that are chiral, which is important for making drugs.
Methodology
The study involved synthesizing α-sulfonylallylic donor precursors and examining their reactions with ethyl crotonate to assess diastereoselectivity.
Digital Object Identifier (DOI)
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