Synthesis of Optically-Active Isoquinoline and Indole Alkaloids Employing the Pictet-Spengler Condensation with Removable Chiral Auxiliaries Bound to Nitrogen

TEODORO SAUL KAUFMAN

New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles

Research Signpost

Lugar: Trivandrum; Año: 2005; p. 99 - 147

    The diastereoselective Pictet-Spengler synthesis is one of the currently most important synthetic methodologies for the preparation of polysubstituted optically active tetrahydroisoquinolines and tetrahydro- â-carboline derivatives functionalized on  C-1. The Pictet-Spengler condensation with the aid of removable chiral auxiliaries constitutes an interesting approach towards this goal, as summarized in this review. Strategies covered include the use of privileged cyclohexyl-based chiral auxiliaries, optically active N-sulfinyl derivatives, sulfoxides and sulfones, as well as chiral benzylic amines and aminoacids.â-carboline derivatives functionalized on  C-1. The Pictet-Spengler condensation with the aid of removable chiral auxiliaries constitutes an interesting approach towards this goal, as summarized in this review. Strategies covered include the use of privileged cyclohexyl-based chiral auxiliaries, optically active N-sulfinyl derivatives, sulfoxides and sulfones, as well as chiral benzylic amines and aminoacids.