The desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael reaction of N-(tert-butoxycarbonyl)- 3-phenyloxindoles leading to the corresponding axially chiral succinimides in high yields. The use of a squaramide cinchonidine organocatalyst was fundamental to achieve the simultaneous remote control of the stereogenic axis and adjacent quaternary and tertiary stereocenters.

Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters

DI IORIO, NICOLA;SOPRANI, LORENZO;CROTTI, SIMONE;MAROTTA, EMANUELA;MAZZANTI, ANDREA;RIGHI, PAOLO;BENCIVENNI, GIORGIO
2017

Abstract

The desymmetrization of N-(2-tert-butylphenyl)maleimides was realized by means of a Michael reaction of N-(tert-butoxycarbonyl)- 3-phenyloxindoles leading to the corresponding axially chiral succinimides in high yields. The use of a squaramide cinchonidine organocatalyst was fundamental to achieve the simultaneous remote control of the stereogenic axis and adjacent quaternary and tertiary stereocenters.
Di Iorio, Nicola; Soprani, Lorenzo; Crotti, Simone; Marotta, Emanuela; Mazzanti, Andrea; Righi, Paolo; Bencivenni, Giorgio
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/590692
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