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  • Title: Organocatalytic enantioselective construction of multi-functionalized spiro oxindole dienes.
    Author: Huang XF, Zhang YF, Qi ZH, Li NK, Geng ZC, Li K, Wang XW.
    Journal: Org Biomol Chem; 2014 Jul 07; 12(25):4372-85. PubMed ID: 24840651.
    Abstract:
    A diastereo- and enantio-selective domino Michael-cyclization-tautomerization reaction of isatylidene malononitriles with α,α-dicyanoalkenes catalyzed by a cinchona alkaloid-derived bifunctional thiourea catalyst has been developed. A series of multi-functionalized spiro oxindole diene derivatives have been obtained in good to excellent yields (up to 97%) with good to excellent enantioselectivities (up to 96%) as well as good diastereoselectivities (up to 7.9 : 1). In addition, an anomalous temperature effect on the enantioselectivity has also been studied for this transformation.
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