Journal article
Authors list: Zonker, Benjamin; Becker, Jonathan; Hrdina, Radim
Publication year: 2021
Pages: 4027-4031
Journal: Organic & Biomolecular Chemistry
Volume number: 19
Issue number: 18
ISSN: 1477-0520
eISSN: 1477-0539
DOI Link: https://doi.org/10.1039/d1ob00471a
Publisher: Royal Society of Chemistry
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.
Citation Styles
Harvard Citation style: Zonker, B., Becker, J. and Hrdina, R. (2021) Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework, Organic and Biomolecular Chemistry, 19(18), pp. 4027-4031. https://doi.org/10.1039/d1ob00471a
APA Citation style: Zonker, B., Becker, J., & Hrdina, R. (2021). Synthesis of noradamantane derivatives by ring-contraction of the adamantane framework. Organic and Biomolecular Chemistry. 19(18), 4027-4031. https://doi.org/10.1039/d1ob00471a
