Abstract
The first general approach toward the asymmetric synthesis of 4-alkyl-4-carboxy-2-azetidinones derived from amino acids is described. The stereoselective construction of the β-lactam ring was achieved through base-mediated intramolecular cyclization of the corresponding Nα-chloroacetyl derivatives bearing (+)- or (−)-10-(N,N-dicyclohexylsulfamoyl)isoborneol as chiral auxiliary (ee up to 82%).
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