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Author Notes:
Correspondence: Albert Padwa; Phone: 404-727-0283; Fax: 404-727-6629; Email: chemap@emory.edu
Acknowledgments: Dedicated to Csaba Szántay on the occasion of his 80th birthday and for his many contributions to the field of alkaloid chemistry.
Subjects:
Research Funding:
We greatly appreciate the financial support provided by the National Institutes of Health (GM 059384) and the National Science Foundation (Grant CHE-0450779).
Keywords:
- α-diazo dihydroindolinones
- rhodium(II)
- synthesis
- carbenoid
- intramolecular
- dipolar cycloaddition
- azapentacycles
The Rhodium(II) Carbenoid Cyclization-Cycloaddition Cascade of α-Diazo Dihydroindolinones for the Synthesis of Novel Azapolycyclic Ring Systems
Abstract:
Tandem carbonyl ylide formation-1,3-dipolar cycloaddition of α-diazo N-acetyl-tetrahydro-β-carbolin-1-one derivatives occur efficiently in the presence of a dirhodium catalyst to afford bimolecular cycloadducts in high yield. The Rh(II)-catalyzed reaction also takes place intramolecularly to give products derived from trapping of the carbonyl ylide dipole with a tethered alkene. The power of the intramolecular cascade sequence is that it rapidly assembles a pentacyclic ring system containing three new stereocenters and two adjacent quaternary centers stereospecifically in a single step and in high yield.
Copyright information:
© 2007 Elsevier Ltd. All rights reserved.
This is an Open Access work distributed under the terms of the Creative Commons Attribution-NonCommerical-NoDerivs 3.0 Unported License (http://creativecommons.org/licenses/by-nc-nd/3.0/).
