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. - In: SYNTHESIS. - ISSN 1764-6103. - STAMPA. - 49:(2017), pp. 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.
