Multicomponent synthesis of pyrroles from cyclopropanes: a one-pot palladium(0)-catalyzed dehydrocarbonylation/dehydration.

Abstract

Ring the changes: The cycloaddition of nitrones with 1-carboallyloxy-1-carbomethoxycyclopropanes yields tetrahydro-1,2-oxazines, which in turn undergo a Tsuji dehydrocarbonylation to give dihydro-1,2-oxazines (see scheme; dba = dibenzylideneacetone). Addition of base to this reaction mixture results in clean conversion to pyrroles. The result is a flexible three-component strategy for the synthesis of tetrasubstituted pyrroles.

• Authors: William J Humenny, Polydoros Kyriacou, Katarina Sapeta, Avedis Karadeolian, Michael A Kerr
• Journal: Angewandte Chemie (International ed. in English) (Angew Chem Int Ed Engl) Vol. 51 Issue 44 Pg. 11088-91 (Oct 29 2012) ISSN: 1521-3773 [Electronic] Germany
• PMID: 23038065 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Cyclopropanes
• Organometallic Compounds
• Pyrroles
• Palladium

Topics

• Catalysis
• Cyclopropanes (chemistry)
• Dehydration
• Molecular Structure
• Organometallic Compounds (chemistry)
• Palladium (chemistry)
• Pyrroles (chemical synthesis, chemistry)
• Stereoisomerism