Collect. Czech. Chem. Commun.
2003, 68, 975-1006
https://doi.org/10.1135/cccc20030975
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
Abstract
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.
