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

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 fundamenta...

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Published in:Synthesis (Stuttgart) 2017-04, Vol.49 (7), p.1519-1530
Main Authors: Di Iorio, Nicola, Soprani, Lorenzo, Crotti, Simone, Marotta, Emanuela, Mazzanti, Andrea, Righi, Paolo, Bencivenni, Giorgio
Format: Article
Language:English
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0036-1588408