Asymmetric Synthesis of Nortropanes <i>via</i> Rh-Catalyzed Allylic Arylation
Yan Zhang, F. Wieland Goetzke, Kirsten E. Christensen, Stephen P. Fletcher
Abstract
an unexpected kinetic resolution, and the resolved enantiopure allyl chloride can undergo highly enantiospecific reactions with N-, O-, and S-containing nucleophiles. The method was applied in a highly stereoselective formal synthesis of YZJ-1139(1), a potential insomnia treatment that recently completed Phase II clinical trials. Our report represents an asymmetric catalytic method for the synthesis of YZJ-1139(1) and related compounds.
Topics & Concepts
Enantiopure drugAllylic rearrangementChemistryEnantioselective synthesisCatalysisKinetic resolutionArylNucleophileAllyl chlorideStereoselectivityCombinatorial chemistryTropaneChlorideStereochemistryOrganic chemistryAlkylChemical synthesis and alkaloidsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods