106399-67-1Relevant academic research and scientific papers
Asymmetric Synthesis of (1'R,3R,4R)-4-Acetoxy-3(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone and Other 3-(1'-Hydroxyethyl)-2-azetidinones from (S)-(+)-Ethyl 3-Hydroxybutanoate: Formal Total Synthesis of (+)-Thienamycin
Georg, Gunda I.,Kant, Joydeep,Gill, Harpal S.
, p. 1129 - 1135 (2007/10/02)
The synthesis of (1'R,3R,4R)-4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone, an important precursor for synthesis of carbapenems and penems, is detailed.The methodology utilized relies on the addition, cyclization reaction between the dianion of (S)-(+)-ethyl 3-hydroxybutanoate and N-arylaldimines.The syntheses of other useful optically active 3-(hydroxyethyl)-2-azetidinones are presented.A study of factors influencing the stereochemistry in the addition, cyclization reaction for the formation of 3-(1'-hydroxyethyl)-2-azetidinones is detailed.
Stereoselective Synthesis of 3-(1-Hydroxyethyl)-2-azetidinones from 3-Hydroxybutyrates
Georg, Gunda I.
, p. 3779 - 3782 (2007/10/02)
Addition of dianions of 3-hydroxybutyrates to benzylideneaniline result in direct formation of trans S*-3-(1-hydroxyethyl)-1,4-diphenyl-2-azetidinone with 95percent diastereoselectivity.Inversion of the configuration at Cα gives the
