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We report that a subtle balance of carbanion reactivity, leaving group activation, and pK a 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 Yoshida (Tetrahedron Lett. 1978, 19, 367).doi:10.3390/61100845 fatcat:nxhycquwsjcofkiiim5rtxjoey