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Synthesis 1997; 1997(8): 942-948
DOI: 10.1055/s-1997-1275
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Functionalized β-Thiolactams by Lewis Acid Catalyzed Addition of Alkynyl Silyl Sulfides to Azomethines

Wolf-Rüdiger Förster, Rainer Isecke, Carsten Spanka, Ernst Schaumann*
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, D-38678 Clausthal-Zellerfeld, Germany, Fax +49(5323)722858; E-mail: ernst.schaumann@tu-clausthal.de
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Publication Date:
31 December 2000 (online)

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Thiophilic Lewis acids (e.g. zinc iodide) have a pronounced catalytic effect on the formal [2+2] cycloaddition of alkynyl silyl sulfides 2 and Schiff bases 3 to give 2-azetidinethiones 4. In contrast to uncatalyzed reactions, a large number of functionalities is tolerated and yields are significantly improved.

β-thiolactam - Lewis acid catalyzed addition - 2-azetidinethiones - [2+2] cycloaddition

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