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

Naomi Sakai, Nathalie Sordé, Stefan Matile
2001 Molecules  
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