Development of Isomerization and Cycloisomerization with Use of a Ruthenium Hydride with N-Heterocyclic Carbene and Its Application to the Synthesis of Heterocycles
- 26 April 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (11) , 4255-4261
- https://doi.org/10.1021/jo060308u
Abstract
A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.Keywords
This publication has 20 references indexed in Scilit:
- Transition-Metal-Catalyzed Reactions in Heterocyclic SynthesisChemical Reviews, 2004
- A Planning Strategy for Diversity‐Oriented SynthesisAngewandte Chemie International Edition in English, 2003
- Selective Isomerization of a Terminal Olefin Catalyzed by a Ruthenium Complex: The Synthesis of Indoles through Ring‐Closing MetathesisAngewandte Chemie International Edition in English, 2002
- Metathesis of Electron-Rich Olefins: Structure and Reactivity of Electron-Rich Carbene ComplexesOrganometallics, 2002
- Catalytic, Enantioselective Alkylation of α-Imino Esters: The Synthesis of Nonnatural α-Amino Acid DerivativesJournal of the American Chemical Society, 2001
- Construction of Chiral 1,2-Cycloalkanopyrrolidines from L-Proline Using Ring Closing Metathesis (RCM).CHEMICAL & PHARMACEUTICAL BULLETIN, 2000
- New Approaches to Total Synthesis of Manzamine A, Ircinal A and Related Compounds.Journal of Synthetic Organic Chemistry, Japan, 1999
- A Series of Well‐Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR′)(PR3)2] and Its ReactionsAngewandte Chemie International Edition in English, 1995
- Samarium(II) iodide mediated transformation of carbohydrates to carbocyclesJournal of the American Chemical Society, 1989
- Activation of dihydrogen by organo-iridium-phosphido complexes. Evidence for .alpha.-hydrogen abstraction by a terminal phosphide ligandJournal of the American Chemical Society, 1988