2018-Sustainable Industrial Processing Summit
SIPS2018 Volume 2. Amatore Intl. Symp. / on Electrochemistry for Sustainable Development
| Editors: | F. Kongoli, H. Inufasa, M. G. Boutelle , R. Compton, J.-M. Dubois, F. Murad |
| Publisher: | Flogen Star OUTREACH |
| Publication Year: | 2018 |
| Pages: | 216 pages |
| ISBN: | 978-1-987820-84-3 |
| ISSN: | 2291-1227 (Metals and Materials Processing in a Clean Environment Series) |
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Highly Regio and Enantioselective Synthesis of Functionalized Dihydropyridines and One-Pot Synthesis of Pyridines Triggered by Heck Coupling of Monocyclopropanated Heterocycles
Julietta Yedoyan1;1UNIVERSITY OF REGENSBURG, Regensburg, Germany;
Type of Paper: Regular
Id Paper: 350
Topic: 47
Abstract:
Over the last few years, our group has been intrigued by catalytic cyclopropanations of N-Boc-pyrroles, which provides a stereoselective entry into bicyclic donor-acceptor substituted cyclopropanes that can be manipulated in various ways to natural products and synthetically useful building blocks. [1,2]. Herein we report the palladium catalyzed Heck-Mizoroki cross-coupling reaction between monocyclopropanated N-Boc-pyrroles and hetero/aryl halides leading to substituted 1,2-dihydropyridine preparation in moderate to good yields (40-81%). The arylation occurs selectively from the convex face of monocyclopropanated N-Boc-pyrrole, giving 1,2-dihydropyridine with an excellent transfer of chirality. The developed approach offers an attractive general method for accessing important six-membered nitrogen-containing scaffolds, which are in high demand in the pharmaceutical sciences and beyond. [3]
Keywords:
Catalysis; Drug design; Organic chemistry;References:
[1] O. Reiser, Isr. J. Chem. 2016, 56, 531-539[2] L. Pilsl; T. Ertl, and O. Reiser. Org. Lett. 2017, 19, 2754a-2757.
[3] M. Hilton, R. Dolewski, and A. McNally J. Am. Chem. Soc. 2016, 138, 13806-13809