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Imine Substituent Effects on [2+2]Cycloadditions with Ketenes
Author(s) -
Palomo Claudio,
Aizpurua Jesus M.,
Legido Marta,
Galarza Regina,
Deya Pere M.,
Dunoguès Jacques,
Picard Jean Paul,
Ricci Alfredo,
Seconi Giancarlo
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199612391
Subject(s) - substituent , chemistry , trimethylsilyl , imine , alkyl , methylamine , aldimine , medicinal chemistry , cycloaddition , organic chemistry , catalysis
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.