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Herein, we report that under mild and transition-metal-free conditions an unprecedented and practical SN2′ reaction of Morita–Baylis–Hillman adducts with isocyanoacetates takes place in a stereo- and regiospecific manner. This reaction… Click to show full abstract
Herein, we report that under mild and transition-metal-free conditions an unprecedented and practical SN2′ reaction of Morita–Baylis–Hillman adducts with isocyanoacetates takes place in a stereo- and regiospecific manner. This reaction which tolerates a wide variety of functionalities delivers transformable α-allylated isocyanoacetates in high efficiencies. Preliminary studies on the asymmetric version of this reaction indicate that ZnEt2/chiral amino alcohol combinations are an asymmetric catalytic system for this transformation, giving an enantioenriched α-allylated isocyanoacetate with a chiral quaternary carbon in a high yield.
Journal Title: ACS Omega
Year Published: 2023
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