One pot, simple, and efficient synthesis of (E)- and (Z)-3-allylidene-β-lactams from 3-allyl-3-phenylseleno-β-lactams: analogues of β-lactamase inhibitors. Issue 42 (19th October 2016)

• Record Type: Journal Article
• Authors: Bhalla, Aman; Bari, Shamsher S.; Vats, Sunil; Bhalla, Jitender; Sharma, Kiran; Narula, Dipika
• Is Part Of: Tetrahedron letters. Volume 57:Issue 42(2016)
• Page Start: 4763
• Page End: 4766
• Publication Date: 2016-10-19
• Subjects: β-Lactams -- 3-Allylidene-β-lactams -- 3-Allyl-3-phenylseleno-β-lactams -- Oxidation -- β-Elimination; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.043
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Exploration of oxidation and β-elimination in one step. Stereoselective synthesis of ( E )-3-allylidene-β-lactams. Simple, efficient, fast (12–18 min) methodology to earlier reported ones (12–90 h). Use of dichloromethane as solvent in place of unsafe carbon tetrachloride. 3-Allyl-3-phenylseleno-β-lactams: versatile & easily prepared substrates. Abstract: The direct synthesis of ( E )- and ( Z )-3-allylidene-β-lactams from 3-allyl-3-phenylseleno-β-lactams under mild conditions has been described. 3-Allyl-3-phenylseleno-β-lactams acts as an efficient substrate for in situ oxidation and elimination in one step. This method is simple, convenient, fast, and very efficient.