Recent advances in the development of highly enantioselective synthetic methods

Abstract

In the course of the development of modern synthetic methods in the field of asymmetric synthesis the SAMP-/RAMP-hydrazone method opens a highly diastereo-and enantioselective route to a great variety of carbonyl compounds, alcohols, amines and heterocycles. In this paper recent advances in the development of biomimetic C-C bond formations, such as the synthesis of C2-symmetric ketodiols, polyhydroxylated piperidines (azasugars), HIV-1 protease inhibitors (AIDS), and the first chiral phosphoenol pyruvate (PEP) equivalent, will be reported. Furthermore, efficient and highly stereoselective 1,2-additions to the CN double bond of hydrazones and imines give rise to various amine compounds of high enantiomeric purity. Asymmetric Michael initiated ring closure (MIRC) reactions afford trans-disubstituted cycloalkanoates with virtually complete control of three contiguous stereogenic centers. Finally, chirality transfer processes mediated by organo iron and palladium complexes allow allylic substitutions with virtually complete regioselectivity and chirality transfer both under stoichiometric (Fe) and catalytic (Pd) conditions.