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, N., Soprani, L., Crotti, S., Marotta, E., Mazzanti, A., Righi, P., et al. (2017). Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters. SYNTHESIS, 49, 1519-1530 [10.1055/s-0036-1588408].
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
