… 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: …

GI Georg, J Kant, HS Gill

Index: Georg, Gunda I.; Kant, Joydeep; Gill, Harpal S. Journal of the American Chemical Society, 1987 ,  vol. 109,  # 4  p. 1129 - 1135

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Citation Number: 129

Abstract

Abstract: The synthesis of (l'R, 3R, 4R)-4-acetoxy-3-(l'-((tert-butyldimethylsilyl) oxy) ethyl)-2- azetidinone, an important precursor for the 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 ...