Synthesis p. 886 - 890 (1997)
Update date:2022-08-03
Topics:
Cainelli, Gianfranco
Giacomini, Daria
Galletti, Paola
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.
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