One-pot conversion of carbamates of unsaturated β-aminoesters into unsaturated β-lactams by use of trimethylsilyl iodide

GRAPHICAL ABSTRACT

ABSTRACT

Trimethylsilyl iodide (TMSI) is introduced as an efficient reagent for the one-pot and direct transformation of carbamates of unsaturated β-aminoesters into the corresponding α-methylene-β-lactams and α-arylidene-β-lactams. The mild reaction conditions, excellent yields and easy work-up procedures make it a useful alternative to previously applied procedures for the rapid synthesis of β-lactams from easily available Baylis-Hillman adducts.

KEYWORDS:

• Baylis–Hillman adducts
• carbamates
• unsaturated β-aminoesters
• α-methylene-β-lactams
• α-arylidene-β-lactams
• trimethysilyl iodide

Funding

The authors are grateful to the Research Council of the University of Guilan for financial support of this research work.