%0 Journal Article
%T Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
%A Naomi Sakai
%A Nathalie Sord¨¦
%A Stefan Matile
%J Molecules
%D 2001
%I MDPI AG
%R 10.3390/61100845
%X 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 Yoshida (Tetrahedron Lett. 1978, 19, 367).
%K Bioorganic chemistry
%K Claisen condensation
%K enzyme mimics
%K polyketide synthesis
%U http://www.mdpi.com/1420-3049/6/11/845