The role of imine-enamine tautomerism in effecting cross-aldol condensations |
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Authors: | James H Babler Matthew C Atwood Jonathan E Freaney Anthony R Viszlay |
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Institution: | Department of Chemistry, Loyola University of Chicago, Chicago, IL 60626, United States |
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Abstract: | An indirect method to effect cross-aldol coupling of two nonequivalent enolizable aldehydes is reported that involves initial conversion of one aldehyde to an imine derivative possessing an N-3° alkyl substituent. In sharp contrast to the related couplings (e.g., the use of α-lithiated imines at low temperature), condensation between the imine and several representative aldehydes occurs readily at ambient temperature in the presence of a catalytic amount of cobalt(II) chloride. |
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