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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)