Abstract
3-Alkoxy/aryloxy-β-lactams are synthesized in satisfactory to good yields from the reaction of imines and alkyl/aryl diazoacetates under photoirradiation conditions. Typically, trans-β-lactams are obtained as the major products from linear imines using the current method. By contrast, the corresponding thermal reaction of imines and alkoxy/aryloxyacetyl chlorides, or their equivalents, in the presence of triethylamine affords cis-β-lactams as the major or exclusive products. The formation of trans-β-lactams from linear imines is attributed to isomerization of the imines from their trans-isomers into syn-isomers under UV irradiation. The reported method represents a metal-free and neutral approach for the synthesis of 3-alkoxy/aryloxy-β-lactams.
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