Bioinspired metal-catalysed Doebner-Knoevenagel condensations between malonic acid half thioesters and aldehydes

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. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).