Journal article

Publication year: 2015

Pages: 6231-6236

Journal: European Journal of Organic Chemistry

Volume number: 2015

Issue number: 28

ISSN: 1434-193X

eISSN: 1099-0690

DOI Link: https://doi.org/10.1002/ejoc.201500691

Publisher: Wiley

Abstract: 
We present a new approach to disubstituted diamondoids from corresponding carboxylic acids. A dirhodium-acetate-catalyzed (1 mol-%) nitrene insertion reaction of sulfamides was, for the first time, applied to intramolecular C-H functionalization reactions of rigid tricyclic frameworks. This straightforward approach enables the effective and regio-selective synthesis of a variety of diamondoid-based cyclic sulfamidates, which are synthetically valuable building blocks. Reductive deprotection of the sulfamidate moiety leads to corresponding 1,3-amino alcohol derivatives. Oxidation of the sulfamidate moiety by KMnO4 provides access to 1,3-keto alcohols or imines. Finally, we report the synthesis of Vildagliptin (R) analogues as new antidiabetic drug candidates (DPP-4 inhibitors).

Harvard Citation style: Hrdina, R., Metz, F., Larrosta, M., Berndt, J., Zhygadlo, Y., Becker, S., et al. (2015) Intramolecular C-H Amination Reaction Provides Direct Access to 1,2-Disubstituted Diamondoids, European Journal of Organic Chemistry, 2015(28), pp. 6231-6236. https://doi.org/10.1002/ejoc.201500691

APA Citation style: Hrdina, R., Metz, F., Larrosta, M., Berndt, J., Zhygadlo, Y., Becker, S., & Becker, J. (2015). Intramolecular C-H Amination Reaction Provides Direct Access to 1,2-Disubstituted Diamondoids. European Journal of Organic Chemistry. 2015(28), 6231-6236. https://doi.org/10.1002/ejoc.201500691