Synthesis and reactivity of sulfur and silyl substituted α-alkylidene-β-lactams

✍ Scribed by John D. Buynak; M.Narayana Rao; Ramalakshmi Yegna Chandrasekaran; Elizabeth Haley; Patrice de Meester; Shirley C. Chu

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 202 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80837-6

✦ Synopsis

Synthetically valuable cc-alkylidene-B-lactams are produced from the addition of chlorosulfonyl isocyanate to allenyl sulfides. Recently, several cr-alkylidene-B-lactams have been shown to be potent B-lactamase inhibitors. Included are the asparenomycins' (l), Ro 15-1903' (Z), and 6-r(L)-methoxymethylenelpenicillanic acid3 (z= We recently initiated a program to explore the addition of chlorosulfonyl isocyanate to functionalized allenes with the goal of producing a-alkylidene-B-lactams with synthetic potential.4 While CSI is a valuable reagent for the one step conversion of olefins to B-lactams,5 the high reactivity of this reagent often precludes addition