Diastereoselective addition of chlorotitanium enolates of N-acyl thiazolidinethione to activated imines — A novel synthesis of β-lactams

Authors: Herold-Dublin, Marike; Liotta, Dennis C.

Source: Canadian Journal of Chemistry, Volume 84, Number 12, December 2006 , pp. 1696-1699(4)

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Abstract:

We report a novel methodology for preparing enantiomerically pure β-lactams, starting from nitriles in diastereomeric ratios up to 10:1. The power of the methodology was demonstrated by the efficient synthesis of the cholesterol absorption inhibitor SCH 48462.Key words: β-lactam, N-metalloaldimine, titanium Lewis acids, cholesterol absorption inhibitor.

Nous rapportons une nouvelle méthode de préparation des β-lactames énantiomériquement pures à partir de nitriles avec des rapports diastereomériques allant jusqu'à 10 : 1. L'efficacité de la méthode a été démontrée par la synthèse de l'inhibiteur d'absorption du cholestérol SCH 48462.Mots clés : β-lactame, N-metalloaldimine, acides de Lewis à base de titane, inhibiteur d'absorption du cholestérol.[Traduit par la Rédaction]

Document Type: Research article

Publication date: 2006-12-01

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