<i>cis</i>-Diastereoselective Synthesis of Spirooxindolo-ß-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent.

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

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

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

Afiliación

Filatov VE; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Kuznetsova J; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Petrovskaya L; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Yuzabchuk D; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Tafeenko VA; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Zyk NV; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.
Beloglazkina EK; Department of Chemistry, Lomonosov Moscow State University, Leninskie gory 1/3, 119991 Moscow, Russian Federation.

ACS Omega ; 6(35): 22740-22751, 2021 Sep 07.

Article en En | MEDLINE | ID: mdl-34514245

ABSTRACT

ABSTRACT

A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-ß-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 ß-lactam formation for all tested phenylacetic acids except 4-MeOC6H4CH2COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: ACS Omega Año: 2021 Tipo del documento: Article