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Reaction of dimethyl 1,3-acetonedicarboxylate 8 with oxalylchloride 2 and magnesium chloride as catalyst yielded 2,3-dioxo-2,3-dihydrofuran 9, which is in equilibrium with tautomer 10 (9:10 = 1:2). Addition of thionyl chloride to a mixture of 9/10 afforded 3-chloro-2(5H)-furanone 11. The structure of 11 was unequivocally established by X-ray diffraction, which indirectly proved the structure of 10 as well. Ring opening of 11 by nucleophilic attack with benzylamine 14 in C2-position and subsequent recyclization led to racemic 3-chloro-5-hydroxy-2-oxo-2,5-dihydropyrrole 15. According to a single crystal X-ray analysis, 15 aggregates via stereospecific self selection through hydrogen bonds to give chiroselectively the one-dimensional strands  ∞  1 [(S)-15] and  ∞  1 [( R)-15]

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Synthese und Aggregatbildung eines 5-Hydroxy-2,5-dihydropyrrols. Enantiomerenreine, eindimensionale Stränge durch Wasserstoffbrückenbindungen und chiroselektive Selbstorganisation/Synthesis and Aggregation of a 5-H ydroxy-2,5-dihydropyrrole. Enantiomerically Pure, One-dimensional Strands via Hydrogen Bonds and Chiroselective Self Organization