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

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.

SUBMITTER: Filatov VE

PROVIDER: S-EPMC8427784 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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

Filatov Vadim E VE Kuznetsova Juliana J Petrovskaya Lada L Yuzabchuk Dmitry D Tafeenko Victor A VA Zyk Nikolay V NV Beloglazkina Elena K EK

ACS omega 20210826 35

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-MeOC6H4CH ...[more]

PMID: 34514245

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