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

A competent synthetic route for the synthesis of novel ( Z)- and ( E)-3-allylidene-β-lactams is described. The strategy involves oxidation of trans-3-allyl-3-phenylthio-β-lactams 1 using sodium metaperiodate (NaIO 4) to diastereomeric trans-3-allyl-3-phenylsulfinyl-β-lactams 2 and 3, which further u...

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Bibliographic Details
Published in:Tetrahedron letters 2010-03, Vol.51 (13), p.1719-1722
Main Authors: Bari, Shamsher S., Arora, Renu, Bhalla, Aman, Venugopalan, Paloth
Format: Article
Language:English
Subjects:
3-Allylidene-β-lactams
Thermolysis
trans-3-Allyl-3-phenylsulfinyl-β-lactams
β-Elimination
β-Lactam
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Summary:A competent synthetic route for the synthesis of novel ( Z)- and ( E)-3-allylidene-β-lactams is described. The strategy involves oxidation of trans-3-allyl-3-phenylthio-β-lactams 1 using sodium metaperiodate (NaIO 4) to diastereomeric trans-3-allyl-3-phenylsulfinyl-β-lactams 2 and 3, which further undergo thermal β-elimination in refluxing carbon tetrachloride to furnish ( Z)- and ( E)-3-allylidene-β-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.01.085