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A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting γ-lactam can be readily converted into a novel proline analogue.

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Auf dem im Formelschema angegebenen Weg wurden die Prostaglandine (VIII) und (X) hergestellt.

The reaction of benzyl malonic esters with hydrazine allows a convenient and stereoselective access to the (R)‐γ‐lactam (IV).

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Die Hydrolyse der Benzothiadiazine (I), der sog. "Hydrochlorthiazide", die als Diuretica Bedeutung haben, wurde als Funktion des pH‐Wertes untersucht.