Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 7, Pages 2897-2907Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo302655u
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An asymmetric organocatalytic one-pot synthesis of six-membered spirocyclic oxindoles has been successfully developed through a relay Michael/Michael/aldol addition reaction catalyzed by the combination of readily available diphenylprolinol silyl ether and bifunctional quinine thiourea. The one-pot protocol affords the highly substituted spirocydic oxindoles in high yields and perfect enantioselectivities. More importantly, through judicious choice of the organocatalysts employed, this reaction could be readily adapted to predominantly afford an alternative major diastereomer of the product.
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