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We report that a subtle balance of carbanion reactivity, leaving group activation, and pKa of the catalyst is required for efficient self-condensation of thiomalonates to thioacetoacetates in up to 71% yield under “biomimetic” conditions originally proposed by Kobuke and Yoshid

Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?