Remote control of the axial chirality of N-(2-t-butylphenyl)succinimides was realized via the vinylogous Michael addition of 3-substituted cyclohexenones to N-(2-t-butylphenyl)maleimides. 9-Amino(9-deoxy)epi-quinine promoted the enantioselective desymmetrization, leading to atropisomeric succinimides with two adjacent stereocenters.
The spiro saga goes on! The title reaction sequence provides the first enantioselective synthesis of spiro nitrocyclopropyl oxindoles. The method provides easy access to these new, biologically inspired compounds from readily available starting materials (see scheme).
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