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Asymmetric Decarboxylative Allylation of Oxindoles

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Publication details

JournalOrganic Letters
DatePublished - 19 Aug 2011
Issue number16
Volume13
Number of pages4
Pages (from-to)4264-4267
Original languageEnglish

Abstract

An asymmetric decarboxylative palladium-catalyzed allylation of alkyl- and aryl-substituted oxindoles has been developed, enabling the installation of an all-carbon quaternary chiral center at the oxindole 3-position in excellent yields and good to excellent enantioselectivity. An intriguing substrate-dependent reversal in stereoselectivity has been observed, whereby the size of the substituent determines the facial selectivity in the allylation step.

    Research areas

  • ENANTIOSELECTIVE ALLYLIC ALKYLATION, PALLADIUM-CATALYZED ALLYLATION, QUATERNARY CARBON CENTERS, 3-ALLYL-3-ARYL OXINDOLES, TSUJI ALLYLATION, ENOL CARBONATES, WORKING MODEL, C-H, KETONES, STEREOCENTERS

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