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Molecules 2001, 6(11), 845-851; doi:10.3390/61100845
Article

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

,  and *
Department of Organic Chemistry, University of Geneva, CH-1211 Geneva 4, Switzerland
* Author to whom correspondence should be addressed.
Received: 3 September 2001 / Revised: 15 October 2001 / Accepted: 16 October 2001 / Published: 31 October 2001
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Abstract

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).
Keywords: Bioorganic chemistry; Claisen condensation; enzyme mimics; polyketide synthesis Bioorganic chemistry; Claisen condensation; enzyme mimics; polyketide synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Sakai, N.; Sordé, N.; Matile, S. Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? Molecules 2001, 6, 845-851.

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