2018 - Sustainable Industrial Processing Summit & Exhibition
4-7 November 2018, Rio Othon Palace, Rio De Janeiro, Brazil
| 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; PAPER: 350/Electrochemistry/Regular (Oral) SCHEDULED: 16:20/Wed./Copacabana B (150/1st) 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] 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 |
