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Selectively N‐Protected Enantiopure 2,5‐Disubstituted Piperazines: Avoiding the Pitfalls in Solid‐Phase Fukuyama–Mitsunobu Cyclizations |
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| Authors: | Lars K. Ottesen Christian A. Olsen Dr. Matthias Witt Dr. Jerzy W. Jaroszewski Prof. Henrik Franzyk Prof. |
| Affiliation: | 1. Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen (Denmark), Fax: (+45)?46336041;2. Present address: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA);3. Bruker Daltonik GmbH, Fahrenheitstrasse 4, 28359 Bremen (Germany) |
| Abstract: | Robust protocol! A diverse array of piperazine scaffolds was obtained by a robust solid‐phase‐synthesis protocol involving multistep elaboration of a resin‐bound aziridine (see scheme). Microwave‐assisted on‐resin protectinggroup introduction and manipulation as well as intramolecular Fukuyama–Mitsunobu cyclization conditions were key features.  |
| Keywords: | aminolysis aziridines Fukuyama– Mitsunobu cyclization piperazines solid‐phase synthesis |