113791-23-4Relevant academic research and scientific papers
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 (1987)
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.
Catalytic imine-imine cross-coupling reactions
Matsumoto, Masatoshi,Harada, Masashi,Yamashita, Yasuhiro,Kobayashi, Shu
supporting information, p. 13041 - 13044 (2015/01/16)
We report here efficient catalytic imine-imine cross-coupling reactions based on an umpolung strategy; an imine bearing a 9-fluorenyl moiety on its nitrogen atom, which acted as a nucleophile, reacted with another imine to afford an imine-imine cross-coupling adduct in high yield. Furthermore, a chiral guanidine acted as a chiral catalyst for these coupling reactions, and optically active 1,2-diamines were obtained in high yields with high enantioselectivities. This journal is
STEREOSELECTIVE ONE-POT SYNTHESES OF TRANS-3-AMINO-β-LACTAMS FROM ZINC ENOLATES OF N-PROTECTED α-AMINOACID ESTERS AND IMINES
Steen, Fred H. van der,Jastrzebski, Johann T.B.H.,Koten, Gerard van
, p. 2467 - 2470 (2007/10/02)
A new one-pot synthesis of 3-amino-β-lactams that is based on the condensation of simple imines with zinc enolates of disilyl protected glycine esters is reported.Isolated yields are high and a trans-selectivity is observed.
