Asymmetric Synthesis of Fluoroalkyl Amino Compounds via Chiral Sulfoxides

A wide range of biologically interesting, structurally diverse, chiral and stereochemically defined fluoro-amino compounds have been synthesized in nonracemic form, exploiting the manifold reactivity of the stereogenic sulfinyl group, as a primary source of chirality. Fluorinated and fluoroalkylated analogs of chiral amines, beta-amino alcohols, tx-amino acids, beta-hydroxy alpha-amino acids, beta-amino alpha-hydroxy acids, gamma-amino beta-hydroxy acids, ephedra and tetrahydroisoquinoline alkaloids were stereoselectively obtained from easily available and nonexotic starting materials, such as fluorinated acetic or pyruvic esters, a cheap and easy-to-handle source of fluorine. Some new asymmetric reactions disclosed during the latest five years are described.