From synthetic methods to γ-peptides -from chemistry to biology

Abstract

The research activities of our group are demonstrated by examples in the following fields: (i) TADDOL auxiliary system (combinatorial synthesis, a chiral hydroperoxide, immobilization on controlled-pore glass silica gel); (ii) a geminally diphenyl-substituted 4-isopropyl-1,3-oxazolidinone as a superior Evans-type auxiliary (for enantioselective enolate alkylation, aldol addition, Michael addition, and Diels-Alder reactions); (iii) enantioselective reactivity umpolung (with a lithiated methylthiomethyl derivative of an oxazolidinone), and (iv) chemical and biological investigations of γ-peptides (folding to helices and turns, stability against peptidases). The impact of biology on the projects of a synthetic organic group is discussed.