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
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Sprache:eng
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asymmetric syntheses
cycloadditions
imines
β-lactams
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container_end_page 1241
container_issue 11
container_start_page 1239
container_title Angewandte Chemie International Edition
container_volume 35
creator Palomo, Claudio
Aizpurua, Jesus M.
Legido, Marta
Galarza, Regina
Deya, Pere M.
Dunoguès, Jacques
Picard, Jean Paul
Ricci, Alfredo
Seconi, Giancarlo
description 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.
doi_str_mv 10.1002/anie.199612391
format Article
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subjects asymmetric syntheses
cycloadditions
imines
β-lactams
title Imine Substituent Effects on [2+2]Cycloadditions with Ketenes
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