Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 49, Pages 17595-17599Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604616
Keywords
asymmetric catalysis; high-throughput screening; mass spectrometry; Morita-Baylis-Hillman; organocatalysis
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Funding
- Swiss National Science Foundation
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An efficient protocol for the evaluation of catalysts for the asymmetric Morita-Baylis-Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of methyl acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate-and enantioselectivity-determining.
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