Synthesis of hindered chiral guanidine bases starting from (S)-(N,N-dialkyl-aminomethyl)pyrrolidines and BrCN |
| |
| Institution: | 1. Institut für Organische Chemie und Makromolekulare Chemie der Friedrich-Schiller-Universität, Humboldtstrasse 10, D-07743 Jena, Germany;2. Institut für Anorganische und Analytische Chemie der Friedrich-Schiller-Universität, Lessingstrasse 8, D-07743 Jena, Germany;1. Dip. di Chimica dell''Università degli Studi di Milano, via Golgi, 19, I-20133 Milano, Italy;2. UdR di Milano dell''INSTM, via Golgi, 19, I-20133 Milano, Italy;3. Istituto di Scienze e Tecnologie Molecolari del CNR, via Golgi, 19, I-20133 Milano, Italy;4. Institut des Sciences Chimiques de Rennes UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 35042 Rennes Cedex, France;1. Department of Chemistry and Biochemistry, 700 Planetarium Place, University of Texas at Arlington, TX 76019, USA;2. Life and Health Sciences Department, 7400 University Hills Blvd, University of North Texas at Dallas, Dallas, TX 75241, USA;1. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah 711103, India;2. Centre for Health Science and Technology, Indian Institute of Engineering Science and Technology, Shibpur, Howrah 711103, India;3. Department of Chemistry, Jadavpur University, Kolkata 700032, India;4. X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia;5. Department of Pharmaceutical Chemistry College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia |
| |
| Abstract: | An efficient method for the preparation of hindered chiral guanidines using cyanogen bromide is described. The reaction between BrCN and vicinal diamines derived from (S)-2-(N,N-dialkyl-aminomethyl)-pyrrolidines provides chiral substituted cyanamides. The cyanamide derivatives reacted with secondary amines in hexafluoroisopropanol at reflux to form chiral hindered guanidines, which were isolated in good to excellent yields (70–96%). The chiral guanidines were prepared in an effort to design sophisticated chiral guanidine catalysts for asymmetric synthesis. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
