Synthesis of Halohydrin‐ and Haloallyl‐ Linked Novel β‐lactam Derivatives

ABSTRACT The β‐lactam scaffold has played a pivotal role in medicinal chemistry due to its extensive application in antibiotic development. The presence of β‐lactam rings attached to a variety of appendages in several widely used antibiotics has always kept this area of research open to new explorations. With the aim to expand the library of variously substituted novel β‐lactams, the reported work has been carried out. In the present study, novel 1,2‐halohydrin and haloallyl‐linked β‐lactam derivatives were synthesized from 3‐allyl‐3‐phenylsulfinyl‐β‐lactams in excellent yields. The olefinic bond of the substrate was successfully functionalized to generate halohydrin and allylic halide moieties at the C‐3 position. Optimized reaction conditions enabled efficient transformations with high regio‐ and stereoselectivity. Both chloro‐ and bromo‐ substituted derivatives were obtained. All synthesized compounds were thoroughly characterized, and plausible mechanisms for their formation are proposed.