Imine Substituent Effects on [2+2]Cycloadditions with Ketenes

Imine Substituent Effects on [2+2]Cycloadditions with Ketenes

Silicon makes the difference! In contrast to known imines from alkyl‐ or arylamines, imines derived from C,C‐bis(trimethylsilyl)methylamine and enolizable aldehydes react, as shown below, with ketenes to afford exclusively β‐lactams. Furthermore, the reaction is highly diastereoselective when asymme...

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Veröffentlicht in:Angewandte Chemie International Edition 1996-06, Vol.35 (11), p.1239-1241
Hauptverfasser: Palomo, Claudio, Aizpurua, Jesus M., Legido, Marta, Galarza, Regina, Deya, Pere M., Dunoguès, Jacques, Picard, Jean Paul, Ricci, Alfredo, Seconi, Giancarlo
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric syntheses
cycloadditions
imines
β-lactams
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Zusammenfassung:Silicon makes the difference! In contrast to known imines from alkyl‐ or arylamines, imines derived from C,C‐bis(trimethylsilyl)methylamine and enolizable aldehydes react, as shown below, with ketenes to afford exclusively β‐lactams. Furthermore, the reaction is highly diastereoselective when asymmetric ketenes are used.
ISSN:0570-0833
1521-3773
DOI:10.1002/anie.199612391