Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 6, Pages 2077-2087Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0622678
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High enantioselection is obtained in Michael additions of cyclic beta-ketoesters in the presence of lanthanium triflates and (S,S)-ip-pybox. Intermediates based on simultaneous coordination of the lanthanide to both (S,S)-ip-box and beta-ketoester (in keto and enolate forms) are detected by means of ESI mass spectrometry and NMR experiments, and a possible mechanism is proposed through theoretical calculations.
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