Recueil des Travaux Chimiques des Pays-Bas p. 516 - 518 (1987)
Update date:2022-08-17
Topics:
Jastrzebski, Johann T. B. H.
Steen, Fred H van der
Koten, Gerard van
A new route for the high yield synthesis (better then 90 percent) of exclusively trans-β-lactams (azetidin-2-ones) is reported which involves the 1:1 reaction of an α-aminoacid ester zinc enolate with an appropriate imine.The reaction can be carried out as a 'one-pot' synthesis as has been demonstrated for the synthesis of trans-3-diethylamino-4-phenyl azetidin-2-one (93 percent yield).The novel zinc enolates have most likely a Z-geometry as a result of intramolecular chelate coordination.Evidence has been obtained that in the first step these zinc enolates react with the imine in a highly diastereoselective manner providing the threo aldolate which in a subsequent step undergoes ring closure to the azetidin-2-one.
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