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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?

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Received: 3 September 2001; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

Sakai N, Sordé N, Matile S. Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? Molecules. 2001; 6(11):845-851.

Chicago/Turabian Style

Sakai, Naomi; Sordé, Nathalie; Matile, Stefan. 2001. "Mg2+-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?" Molecules 6, no. 11: 845-851.


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