Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide
Abolfazl Hosseini, Peter R. Schreiner*
*Institute of Organic Chemistry, Justus Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany, Email: prsuni-giessen.de
A. Hosseini, P. R. Schreiner, Org. Lett., 2019, 21, 3746-3749.
DOI: 10.1021/acs.orglett.9b01192 (free Supporting Information)
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A convenient Kinugasa reaction protocol enables a one-pot synthesis of 4-substituted β-lactams from inexpensive calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAFˇ3H2O in the presence of CuCl/NMI. The reaction provides rapid access to practical quantities of β-lactams substituted at position 4.
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suggested mechanism of the fluoride/copper-catalyzed Kinugasa Reaction