Bioinspired Metal‐Catalysed Doebner–Knoevenagel Condensations between Malonic Acid Half Thioesters and Aldehydes | Zendy

Berrué Fabrice | Zendy; Antoniotti Sylvain | Zendy; Thomas Olivier P. | Zendy; Amade Philippe | Zendy

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Bioinspired Metal‐Catalysed Doebner–Knoevenagel Condensations between Malonic Acid Half Thioesters and Aldehydes

Author(s) -

Berrué Fabrice,

Antoniotti Sylvain,

Thomas Olivier P.,

Amade Philippe

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200600880

Subject(s) - knoevenagel condensation , chemistry , malonic acid , polyketide , polyketide synthase , catalysis , metal , organic chemistry , biomimetic synthesis , biosynthesis , enzyme

Inspired by polyketide biosynthesis, unprecedented metal‐catalysed Doebner–Knoevenagel condensations between Malonic Acid Half Thioesters (MAHTs) and various aldehydes have been achieved through the use of Yb(OTf) 3 as catalyst, mimicking a five‐domain polyketide synthase module for the first time. In the presence of 5‐methoxybenzimidazole, stereo‐ and regiocontrol of the reaction proved to be high. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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