Abstract
The reaction of 2-3- O-isopropylidene- d-glyceraldehyde ( 1) with active methylene compounds in the absence of a catalyst involves facile and reversible addition to the formyl group. The adducts are readily transformed into furan derivatives by acid hydrolysis. When the reaction is catalysed with piperidine, unsaturated products are also formed, including α,β- and β,γ-unsaturated dicarbonyl compounds, which are transformed into furan derivatives via hydrolysis of the acetal group. A new type of unsaturated compound having a spiro-ketal structure is also produced as a result of intramolecular cyclisation.
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