Elucidation of the Complex Baylis-Hillman Reaction of3-Methoxy-2-nitrobenzaldehyde with Methyl Vinyl Ketone

摘要

DABCO-catalyzed reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone (MVK) affords a mixture of products,comprising the ‘normal’ Baylis-Hillman adduct, theMVKdimer and a pair of diastereomeric bis-(MVK)Baylis-Hillman adducts.1HNMRspectroscopy-based kinetic studies have provided clear insights into the competing pathways and product distributionin this complex reaction.