Asymmetric Gold-Catalyzed Cycloisomerization of 1,6-Enynes
Author Information
Author(s): Pradal Alexandre, Chao Chung-Meng, Toullec Patrick Y, Michelet Véronique
Primary Institution: Laboratoire Charles Friedel, UMR 7223, Ecole Nationale Supérieure de Chimie de Paris, Chimie ParisTech
Hypothesis
Can asymmetric gold-catalyzed cycloisomerization of 1,6-enynes produce bicyclo[4.1.0]heptene derivatives with high enantiomeric excess?
Conclusion
The study successfully developed an asymmetric gold-catalyzed cycloisomerization reaction that produces functionalized bicyclo[4.1.0]heptenes with excellent enantiomeric excess.
Supporting Evidence
- The cycloisomerization reactions were highly substrate-dependent.
- Enantiomeric excesses reached up to 99% for some bicyclic derivatives.
- The methodology was successfully applied to the synthesis of pentasubstituted cyclopropyl heterobicycles.
Takeaway
This research shows how to use gold to help make special chemical shapes called bicyclo[4.1.0]heptenes, which can be very pure and useful.
Methodology
The study involved using a chiral gold catalyst and silver salts to perform cycloisomerization reactions of 1,6-enynes in toluene under mild conditions.
Limitations
The reaction yields and enantiomeric excesses were generally lower for nitrogen-tethered enynes compared to oxygen-tethered ones.
Digital Object Identifier (DOI)
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