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A simple and efficient procedure for the stereoselective synthesis of novel monocyclic cis-β-lactams, pharmaceutically fascinating and potential synthons have been developed. The reaction of ketene derived insitu from phenoxyacetyl chloride with tetralone substituted imines resulted in the exclusive formation of monocyclic cis-β-lactams containing 1,3,4-thiadiazole nucleus by [2 + 2] cycloaddition reaction. The structures of all the novel synthesized monocyclic cis-β-lactams were verified using various spectroscopic techniques such as FT-IR, 1 H NMR, 13 C NMR, HRMS, and elemental analysis (CHN). The cis configuration of β-lactams was deduced using the coupling constant (J) value of H-3 and H-4. The prominent features of this work are simple reaction conditions, good yields, easy isolation of products, and no column chromatography separation. All products were obtained by a simple crystallization technique.itors of human cytomegalovirus protein, [15][16] HIV-1 protease, [17] fatty acid synthase, [18] prostate-specific antigen (PSA), [19,20] thrombin, [21] human leukocyte elastase, [22] and cholesterol absorption. [23] Also, other new biological actions of these compounds are potential antimalarial, [24] antifungal, [25][26][27] and [a] M.