The authors acknowledge the NIH-NIGMS (GM 098314) and the University of Michigan Associate Prof. Support Fund for financial support of this work. Additional funding was provided by GlaxoSmithKline and Amgen.
Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas†
Article first published online: 3 JUL 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 35, pages 9247–9250, August 26, 2013
How to Cite
Babij, N. R. and Wolfe, J. P. (2013), Desymmetrization of meso-2,5-Diallylpyrrolidinyl Ureas through Asymmetric Palladium-Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas . Angew. Chem. Int. Ed., 52: 9247–9250. doi: 10.1002/anie.201302720
- Issue published online: 22 AUG 2013
- Article first published online: 3 JUL 2013
- Manuscript Received: 2 APR 2013
- NIH-NIGMS. Grant Number: GM 098314
- asymmetric catalysis;
Lost symmetry: Fused bicyclic ureas are enantioselectively obtained through Pd-catalyzed desymmetrizing carboaminations of meso-2,5-diallylpyrrolidinyl ureas (see scheme). The reactions generate a CN and a CC bond, and afford products with three stereocenters. One of these products was transformed to a tricyclic guanidine and then to 9-epi-batzelladine K over several steps.