BMPD, a novel C2-chiral 1,3-diketone ligand;: Synthesis and application to an asymmetric catalytic reaction

The synthesis of BMPD, 1,3-bis(2-methylferrocenyl)propane-1,3-dione, was achieved via the Claisen condensation of a homochiral ferrocenecarboxylate and an acetylferrocene derived from the same chiral formylferrocene. Several metal complexes were prepared to exemplify the complexation ability of BMPD. A BMPD-yttrium complex was found to act as a new catalyst for silylcyanation of aldehydes with remarkable efficiency. As little as 0.2 mol% of the complex catalyzed the reaction of benzaldehyde and cyanotrimethylsilane to afford the cyanohydrin in 95% yield with 87% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.