Desymmetrization of meso‐2,5‐Diallylpyrrolidinyl Ureas through Asymmetric Palladium‐Catalyzed Carboamination: Stereocontrolled Synthesis of Bicyclic Ureas
Authors:
- 3 July 2013
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 52 (35) , 9247-9250
Abstract
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.Keywords
This publication has 52 references indexed in Scilit:
- Desymmetrisation of meso-diols mediated by non-enzymatic acyl transfer catalystsChemical Society Reviews, 2012
- The chemistry and biology of organic guanidine derivativesNatural Product Reports, 2012
- Recent advances in enantioselective organocatalyzed anhydride desymmetrization and its application to the synthesis of valuable enantiopure compoundsChemical Society Reviews, 2011
- The chemistry and biology of organic guanidine derivativesNatural Product Reports, 2010
- The chemistry and biology of organic guanidine derivativesNatural Product Reports, 2008
- Recent Advances in Catalytic Asymmetric Desymmetrization Reactions2006
- Natural guanidine derivativesNatural Product Reports, 2005
- Inhibition of HIV-1 Envelope-Mediated Fusion by Synthetic Batzelladine AnaloguesJournal of Natural Products, 2004
- Asymmetric Desymmetrization: Simultaneous Stereocontrol of Multi-chiral Centers.Journal of Synthetic Organic Chemistry, Japan, 2002
- Desymmetrization of Prochiral Diesters Via Transition Metal Catalyzed ReactionsIsrael Journal of Chemistry, 1997