Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?

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....

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Detalles Bibliográficos
Autores principales: Sakai, Naomi, Sordé, Nathalie, Matile, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2001
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236409/
http://dx.doi.org/10.3390/61100845
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author Sakai, Naomi
Sordé, Nathalie
Matile, Stefan
author_facet Sakai, Naomi
Sordé, Nathalie
Matile, Stefan
author_sort Sakai, Naomi
collection PubMed
description 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).
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spelling pubmed-62364092018-11-19 Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis? Sakai, Naomi Sordé, Nathalie Matile, Stefan Molecules Article 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). MDPI 2001-10-31 /pmc/articles/PMC6236409/ http://dx.doi.org/10.3390/61100845 Text en © 2001 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Sakai, Naomi
Sordé, Nathalie
Matile, Stefan
Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title_full Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title_fullStr Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title_full_unstemmed Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title_short Mg(2+)-Imidazole-Catalyzed Self-Condensation of Malonyl Thioesters: Getting Tuned for Biomimetic Polyketide Synthesis?
title_sort mg(2+)-imidazole-catalyzed self-condensation of malonyl thioesters: getting tuned for biomimetic polyketide synthesis?
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6236409/
http://dx.doi.org/10.3390/61100845
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