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

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Abstract

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 TBAF·3H₂O 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

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Key Words

β-lactams

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ID: J54-Y2019