Collect. Czech. Chem. Commun. 2003, 68, 975-1006

α-Heterosubstituted Aldehydes in Organic Synthesis. Enantioselective Approaches to New Analogues of Mevinic Acids

Dieter Enders* and Frank Burkamp

Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany


Various aldol approaches towards the asymmetric synthesis of the lactone moiety of HMG-CoA-reductase inhibitors are described. Auxiliary controlled as well as catalytic aldol reactions resulted only in modest to low selectivities, whereas 1,2-additions to readily available highly enantiomerically enriched α-heterosubstituted aldehydes yielded δ-hydroxy-β-ketoesters with a high degree of diastereocontrol and in good chemical yields. The novel mevinic acid analogues could then be obtained by syn-reduction of the addition products.

Keywords: Aldol reactions; Amino aldehydes; Mukaiyama reaction; Stereoselective reactions; Asymmetric synthesis; TADDOL; SAMP; Lactones; HMG-CoA-reductase inhibitors.

References: 117 live references.