The isomeric mixture of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2- and −3-carboxylates (14 and 15), derived from a
proline meso-ionic synthon, demonstrated remarkably different
stabilities towards alkaline hydrolysis. On that basis, a nonchromatographic, highly efficient method for their large-scale
separation was developed. The desired isomer 14 was converted
into 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde, a
key intermediate in the synthesis of bicyclic heteroaryl-substituted 6-alkylidene penems.
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