In continuing our studies on aldol condensation of active methylene compounds, such as dihydrolevoglucosenone, with aromatic five-membered heterocyclic aldehydes, we expanded the original protocol to include substituted aromatic aldehydes. In order to determine the potential effect of electron withdrawing and electron donating groups in aromatic aldehydes over the course of the reaction, we selected several aldehydes as depicted in Scheme 1. The preliminary results indicate that 4-chlorobenzaldehyde is capable of forming an unusual secondary product, a dimer, along with the normal exo-cyclic enone. The dimer structure was determined by 1H and 13C NMR, and simple crystal structure analysis.

Synthesis and reactivity of C-3 carbohydrate exo-cyclic enones

255th National Meeting (2018)

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