Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts
1Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, Linz 4040, Austria.
Abstract:
The first phase-transfer catalyzed cyclopropanation reaction of chalcones using bromomalonates as the nucleophiles in a Michael Initiated Ring Closing reaction (MIRC) was developed. Key to success was the use of a free OH-containing cinchona alkaloid ammonium salt catalyst and carefully optimized liquid/liquid reaction conditions. The reaction performed well for electron neutral and electron deficient chalcones giving the products in yields up to 98% and with enantiomeric ratios up to 91:9.
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