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.
- ENANTIOSELECTIVE ALLYLIC ALKYLATION
- PALLADIUM-CATALYZED ALLYLATION
- QUATERNARY CARBON CENTERS
- 3-ALLYL-3-ARYL OXINDOLES
- TSUJI ALLYLATION
- ENOL CARBONATES
- WORKING MODEL