113830-78-7Relevant articles and documents
Enantioselective Synthesis of 3-Amino-2-azetidinones via the Ester Enolate-Imine Condensation
Steen, Fred H. van der,Kleijn, Henk,Britovsek, George J. P.,Jastrzebski, Johann T. B. H.,Koten, Gerard van
, p. 3906 - 3916 (2007/10/02)
Three approaches to the enantioselective synthesis of 3-amino-4-substituted-2-azetidinones by condensation of α-amino ester enolates with imines are described: (i) application of chiral ester derivatives of N,N-diethylglycine; (ii) application of chiral N
Synthesis and molecular structures of novel α-amino organoaluminum ester enolates. Key intermediates in the selective formation of trans-3-amino-2-azetidinones
Van der Steen,Van Mier,Spek,Kroon,Van Koten
, p. 5742 - 5750 (2007/10/02)
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Selective Formation of 1,3,4-Trisubstituted and 3,4-Disubstituted Trans-β-lactams from Zinc Enolates and Imines
Jastrzebski, Johann T. B. H.,Steen, Fred H van der,Koten, Gerard van
, p. 516 - 518 (2007/10/02)
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.
