Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework
Benjamin Zonker, Jonathan Becker, Radim Hrdina
Abstract
We describe a triflic acid promoted cascade reaction of adamantane derivatives consisting of a decarboxylation of N-methyl protected cyclic carbamates and a subsequent intramolecular nucleophilic 1,2-alkyl shift to generate ring contracted iminium triflates. This reaction expands the family of similar transformations, such as Wagner-Meerwein-, Demjanov-Tiffeneau-, Meinwald- or (semi-)pinacol-rearrangement. It allows the preparation of noradamantane derivatives in a few steps, starting from simple hydroxy-substituted adamantane precursors.
Topics & Concepts
ChemistryIminiumDecarboxylationTriflic acidIntramolecular forceRing (chemistry)AdamantaneNucleophilePinacolStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryIonCatalysisEicosanoids and Hypertension PharmacologySynthesis and Catalytic ReactionsFluorine in Organic Chemistry