A Lewis acid-mediated one-carbon homologation approach to installing a 2-quinolinone core embedded with paraquinone methides, in a high yield of up to 92%, and with high regioselectivity has been developed. Also, post-synthetic modifications, including C−P, C−S, and C−C bond formations, have been demonstrated by the 1,6-addition of suitable nucleophiles. Further, cyclopropanation of 2-quinolinone-embedded p-QM is also demonstrated affording a contiguous quaternary spiro center.
Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.003 Å R factor = 0.061 wR factor = 0.167 Data-to-parameter ratio = 18.0 For details of how these key indicators were automatically derived from the article, see
The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98:2). The practicability of the present methodology...
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