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Synlett 1996; 1996(11): 1103-1105
DOI: 10.1055/s-1996-5690
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Lewis Acid-Promoted Generation of an Iminium ion from Ethyl 2-(N-Benzyloxycarbonylamino)-methylene-3-oxobutanoate and Its Reactions with Ketene Silyl Acetals

Seiki Saito* , Eiji Uedo, Yoshitaka Kato, Yoshinori Murakami, Teruhiko Ishikawa
  • *Department of Bioengineering Science, Faculty of Engineering, Okayama University, Tsushima, Okayama 700, Japan
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Publication Date:
31 December 2000 (online)

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A novel type of nucleophilic addition of ketene silyl acetals (2) to N-acyliminium ion intermediate, which could be generated by the action of catalytic TiCl4 to ethyl 2-(N-benzyloxycarbonylamino)methylene-3-oxobutanoate (1) in CH2Cl2 at -78 °C, has been realized.

Lewis acid - iminium ion - ketene silyl acetal - Mannich reaction

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