Journalartikel

Jahr der Veröffentlichung: 2021

Seiten: 4027-4031

Zeitschrift: Organic & Biomolecular Chemistry

Bandnummer: 19

Heftnummer: 18

ISSN: 1477-0520

eISSN: 1477-0539

DOI Link: https://doi.org/10.1039/d1ob00471a

Verlag: 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.

Harvard-Zitierstil: 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-Zitierstil: 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