Accessing Skeletal Diversity Using Catalyst Control: Formation of n and n + 1 Macrocyclic Triazole Rings
- 30 April 2009
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (11), 2257-2260
- https://doi.org/10.1021/ol900562u
Abstract
A regioselective intramolecular Huisgen cycloaddition was performed on various azido alkyne substrates giving rise to macrocyclic triazole rings. Using catalyst control, a common intermediate has been converted to two structurally unique macrocycles with either a 1,5- or a 1,4-triazole resulting in an n or n + 1 ring size. This is the first example of an intramolecular ruthenium-catalyzed Huisgen cycloaddition.Keywords
This publication has 20 references indexed in Scilit:
- Mo(CO)6- and [Rh(CO)2Cl]2-Catalyzed Allenic Cyclocarbonylation Reactions of Alkynones: Efficient Access to Bicyclic DienedionesOrganic Letters, 2008
- Towards the Optimal Screening Collection: A Synthesis StrategyAngewandte Chemie-International Edition, 2007
- An Approach to Skeletal Diversity Using Functional Group Pairing of Multifunctional ScaffoldsOrganic Letters, 2007
- Drugs for bad bugs: confronting the challenges of antibacterial discoveryNature Reviews Drug Discovery, 2006
- Macrocycloadditions Leading to Conformationally Restricted Small MoleculesOrganic Letters, 2006
- Ruthenium-Catalyzed Cycloaddition of Alkynes and Organic AzidesJournal of the American Chemical Society, 2005
- Allenes and Transition Metals: A Diverging Approach to HeterocyclesOrganic Letters, 2004
- Natural products and combinatorial chemistry: back to the futureCurrent Opinion in Chemical Biology, 2004
- A Planning Strategy for Diversity‐Oriented SynthesisAngewandte Chemie-International Edition, 2003
- Generating Diverse Skeletons of Small Molecules CombinatoriallyScience, 2003