cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent

Vadim E Filatov; Juliana Kuznetsova; Lada Petrovskaya; Dmitry Yuzabchuk; Victor A Tafeenko; Nikolay V Zyk; Elena K Beloglazkina

doi:10.1021/acsomega.1c03063

cis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent

ACS Omega. 2021 Aug 26;6(35):22740-22751. doi: 10.1021/acsomega.1c03063. eCollection 2021 Sep 7.

Authors

Vadim E Filatov¹, Juliana Kuznetsova¹, Lada Petrovskaya¹, Dmitry Yuzabchuk¹, Victor A Tafeenko¹, Nikolay V Zyk¹, Elena K Beloglazkina¹

Affiliation

¹ Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.

Abstract

A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-β-lactams from isatin Schiff bases and substituted phenylacetic acids using ketene-imine cycloaddition reaction with TsCl for a ketene generation has been developed. The reaction procedure does not require absolute solvents and unstable starting reagents. The studied reactions lead to cis-diastereoselective β-lactam formation for all tested phenylacetic acids except 4-MeOC₆H₄CH₂COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.