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The regioselective benzoyloxylation process involves stirring a mixture of phenyl/benzyl-sulfanyl/selenylethanoate  1a-c  with appropriate oxidant [benzoyl peroxide (BPO)  2a /  m -chloroperbenzoic acid ( m -CPBA)  2b  /bis( p -methoxybenzoyl peroxide) (BPM-BPO)  2c ] under catalysis of hydrated copper acetate in toluene at 60 °C/RT. Regioselective C–H functionalization of esters  1a-c  leads to benzoyloxy substituted phenyl/benzyl-sulfanyl/selenylbisesters  3a-g  in good to excellent yields (80–95%). Variably substituted  trans- 3-phenylsulfanyl-β-lactams  4  employed for C3- H  functionalization with BPO  2a  generates diastereoisomeric mixture of  trans-  and  cis -3-benzoyloxy-3-(phenylsulfanyl)-β-lactams  5  and  6  as major and minor isomers after efficient column chromatographic purification. The structural confirmation was done using IR,  1 H NMR,  13 C NMR, DEPT-90 NMR spectroscopic analysis and CHNS elemental analysis.  In vitro  antibacterial and antifungal evaluations on bisesters suggest benzylselenyl-bisester  3c  as potent antimicrobial agent. Out of  trans - and  cis -3-benzoyloxy-β-lactams  5a  and  6a , the  trans  isomer  5a  was active against all microbial strains whereas the  cis  isomer  6a  was completely inactive.

journal of sulfur chemistry

Serendipitous discovery of a regioselective synthesis of novel benzoyloxy substituted phenyl/benzyl-sulfanyl/selenylbisesters, 3-benzoyloxy-3-(phenylsulfanyl)-β-lactams and their antimicrobial evaluation