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Synthesis 1997; 1997(8): 886-890
DOI: 10.1055/s-1997-1276
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Synthesis of N-(Triisopropylsilyl)- and N-(tert-Butyldimethylsilyl)aldimines and Their Application in the Synthesis of β-Lactams

Gianfranco Cainelli1 , Daria Giacomini2 , Paola Galletti
  • 1Dipartimento di Chimica “G.Ciamician”, Via Selmi, 2, I-40126 Bologna, Italy, Fax +39(51)259456; E-mail: cainelli@ciam.unibo.it
  • 2Dipartimento di Chimica “G.Ciamician”, Via Selmi, 2, I-40126 Bologna, Italy, Fax +39(51)259456
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Publication Date:
31 December 2000 (online)

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A new and efficient synthesis of N-(TIPS)imines and N-(TBDMS)-imines starting from enolizable and non-enolizable aldehydes is described. We tested the reactivity of these imines in the preparation of β-lactams. N-(TBDMS)imines effectively give N(-TBDMS)azetidinones with a trans stereochemistry of the ring substituents, complementing N-(TMS)imines which instead afford cis β-lactams. In contrast, N-(TIPS)imines react with ester enolates in few cases because of the extremely low rate of the ring-closure step, so that a decomposition of enolates occurred.

imines - β-lactams - nucleophilic addition - ester enolates - silylimines