Facile synthesis of (Z)- and (E)-3-allylidene-β-lactams via thermal β-elimination of trans-3-allyl-3-sulfinyl-β-lactams

✍ Scribed by Shamsher S. Bari; Renu Arora; Aman Bhalla; Paloth Venugopalan

• Book ID: 104097410
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 328 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.01.085

✦ Synopsis

A competent synthetic route for the synthesis of novel (Z)-and (E)-3-allylidene-b-lactams is described. The strategy involves oxidation of trans-3-allyl-3-phenylthio-b-lactams 1 using sodium metaperiodate (NaIO 4 ) to diastereomeric trans-3-allyl-3-phenylsulfinyl-b-lactams 2 and 3, which further undergo thermal b-elimination in refluxing carbon tetrachloride to furnish (Z)-and (E)-3-allylidene-b-lactams 5 and 6 in good to excellent yields. The molecular structure of 3b has been established with the help of single crystal X-ray analysis.