132127-34-5Relevant articles and documents
A convenient synthesis of the paclitaxel side-chain via a diastereoselective Staudinger reaction
Brown, Stephen,Jordan, Allan M.,Lawrence, Nicholas J.,Pritchard, Robin G.,McGown, Alan T.
, p. 3559 - 3562 (1998)
The N-benzylidene dexivative of (S)-(-)-1-(p-mathoxyphenyl)propyl-1- amine, obtained by a new resolution procedure, exhibits moderate selectivity in the reaction with 2-acetoxyketene; the (S)-(-)-1-(p-methoxyphenyl)propyl group can be oxidatively cleaved from the resultant β-lactam, an important precursor for taxane semi-synthesis.
Beta-lactam synthesis
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Page/Page column 10, (2008/06/13)
The present invention is directed to a process for the preparation of β-lactams. Generally, an imine is cyclocondensed with a ketene acetal or enolate to form the β-lactam product in a "one pot" synthesis, this process is generally performed at a higher temperature than conventional processes.
N,N-dialkylhydrazones as the imine component in the Staudinger-like [2+2] cycloaddition to benzyloxyketene
Fernandez, Rosario,Ferrete, Ana,Lassaletta, Jose M.,Llera, Jose M.,Martin-Zamora, Eloisa
, p. 831 - 833 (2007/10/03)
To overcome the limitations of using unstable imines in Staudinger cycloadditions to ketenes, aldehyde N,N-dialkylhydrazones 1 were used as stable imines. This strategy and a fine tuning of the auxiliary result in a straightforward synthesis of cycloadducts 2, deprotected β-lactams 3, and isoserines 4 (see scheme: a) Et3N, toluene, Δ; b) 1. magnesium monoperoxyphthalate, 2. H2, Pd/C; c) H+).