Cinchona alkaloids allylic substitution

In 2008, Shibata et al. disclosed the first successful catalytic enantioselective fluorination based on the use of cinchona alkaloids. Therefore, it was demonstrated that allyl silanes and silyl enol ethers underwent efficient enantioselective fluorodesilylation with NFSI and a catalytic amount of a bis-cinchona alkaloid in the presence of an excess of base to provide the corresponding fluorinated compounds with an F-substituted quaternary carbon centre with enantioselectivities of up to 95% ee (Scheme 5.3). Furthermore, the authors showed that this catalytic system could be applied to the catalytic 

Chen et al. have found that commercially available modified cinchona alkaloids [(DHQD)2AQN] are outstanding catalysts for the asymmetric allylic alkylation (AAA) reaction of MBH carbonates with a,a-dicyanoolefins 268 or 3-substituted oxindoles 269. Enantioenriched compounds 270 and 271, respectively, with multifunctional frameworks bearing adjacent stereogenic centers were obtained in excellent stereoselectivities (Scheme 3.107). 

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