Journal
TETRAHEDRON LETTERS
Volume 54, Issue 20, Pages 2472-2475Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.095
Keywords
Cyclopropanes; Organocatalysis; Phase-transfer catalysis; Bifunctional; Cinchona alkaloids
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Funding
- Austrian Science Funds (FWF) [P22508-N17]
- Austrian Academy of Sciences at the Institute of Organic Chemistry, JKU Linz
- European Union through the EFRE INTERREG IV ETC-AT-CZ programme [M00146]
- Austrian Science Fund (FWF) [P22508] Funding Source: Austrian Science Fund (FWF)
- Austrian Science Fund (FWF) [P 22508] Funding Source: researchfish
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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. (C) 2013 Elsevier Ltd. All rights reserved.
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